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Holiday Homes in Cape Ann

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    All 153 Rentals in Cape Ann
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    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 26
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill1 / 21
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 42
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Grill
    • Ocean Views
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2016
    The Seaward is the perfect getaway! I travelled from Boston to Rockport to take a little break from the city with my boyfriend. It's about a 50 minute drive or you can take the...
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    About this property
    Formerly Seaward Inn, 'The Seaward' continues to offer a spectacular setting and charming accommodations. Here you can fully relax while listening to the ocean waves. Experience the charm, serenity, and unspoiled beauty that is The Seaward. Suite 205, also known as Gully Point, offers...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Periwinkle Cottage - Unit 11 / 23
    (33)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
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    • Cable/satellite TV
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    June 22, 2018As two old Englanders’ visiting New England we have had a wonderful week here. We last visited 10 years ago in November, so needless to say, the weather has been...
    Reviewed 23 May 2018
    My husband and I rented the cottage for a short getaway after our wedding in Kennebunkport, Maine. After the hubbub of the wedding, it was nice to have this quaint cottage to...
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    About this property
    OPEN YEAR ROUND - 2 night minimum stay. 2018... we're honored to celebrate our 9th year hosting guests from all over the world! PERIWINKLE COTTAGE - truly a place to call 'a home away from home'. This 2-unit, townhouse cottage offers guests privacy and an updated seaside decor with today's...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Outdoor Dining Area
    • Parking
    • Waterfront
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    We all had a wonderful stay at this ocean front home. The home was very clean and comfortable. The location is great! We had 7 people staying and they all loved it there! The...
    Reviewed 6 October 2014
    We rented this quaint, pretty cottage to celebrate a birthday weekend. Our only complaint is that we didn't have more time to spend here. Jennifer was great to work with-very...
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    About this property
    Sitting directly on picturesque Long Beach, this is the perfect spot for a romantic get-away or a family retreat. With decks in the front and back of the house, sun-chasers and shade-seekers alike will be pleased at any time of day. The cottage is sunny and open with a large eat-in kitchen and...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Building was once the historic Sail loft- oozing with character and charm. Inside is a 2 Bedroom, 1 Bath apartment unit. A good sized living area with a leather couch, TV & dining table that can fit up to 6. There is a small patio in front with a table, bench and 2 chairs. Great views of White...
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    01966, Rockport, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Waterfront 2 Bedroom !1 / 14
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 January 2018
    We stayed here for a family wedding in Sept. 2017. The apartment was a perfect location(wedding was 8-mns away). It was very well maintain and very,very clean. (Which is our No...
    Reviewed 2 May 2017
    This apartment is located on the water. When I say "on the water", that's exactly what I mean. At high tide, looking down from the balcony you see water. There are...
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    About this property
    Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around harbor by boat is all within...
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    01930, Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • DVD Player
    • Patio
    • Shared Garden
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2014
    We stayed in this fantastic house for over a week with my husband, my sister and her husband. What a wonderful find and what a beautiful place Rockport is. Cannot recommend it...
    Reviewed 4 August 2014
    We stayed in this lovely two bedroom home for two weeks and enjoyed every minute. The location was convenient to down town and various walking trails as well as the other...
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    About this property
    Rockport, a part of Cape Ann, is one of the most scenic towns in Massachusetts located on Boston’s North Shore, Rockport and nearby Gloucester are filled with attractions: art, music, shopping, beaches, whale watching, boating, fishing, bicycling… you name it! Historic Lexington, Concord & Boston...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Ocean Views
    • Terrace
    • Waterfront
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Seaward offers a spectacular setting and charming accommodations. Loblolly Cove, offers accommodations for up to 4 people. One bedroom has a queen sized bed, while the rather spacious living room has accommodations for two more. At Loblolly Cove, you will enjoy a deck with ocean views and...
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    01966, Rockport, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Quaint Seaside Village Studio Steps  From Beach1 / 12
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2017
    We so much enjoyed this cozy little apartment! It is a great find and well kept with everything you need to enjoy your stay in Rockport. Walk to Bearskin Neck in the heart of...
    Reviewed 21 September 2015
    My husband and I stayed in the studio and loved it. The location is great. You are near all the shops in town and the beach is a block away. The train station is nearby and...
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    About this property
    BOOKING ACCEPTED NOW FOR SUMMER 2018!!. DEDICATED OFF-STREET PARKING FOR ONE CAR. BEST LOCATION IN ROCKPORT steps away from everything! Ground floor studio boasts comfortable and clean efficiency with AC, cable TV and microwave kitchenette, private entrance, private bathroom all on the ground...
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    01966, Rockport, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Captain Quarters1 / 14
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2017
    We stayed for three nights over the July 4th holiday. Perfect location for walking to most places. There is parking right next to the house which is a real bonus in Rockport...
    Reviewed 2 July 2017
    We stayed in the Captain's Quarters of Changing Tides Bed and Breakfast for four nights. THe room's skylight greeted us each morning with blue skies filtered through the...
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    About this property
    Captain's Quarters,at Changing Tides Bed and Breakfast, features a queen-sized bed, two skylights and a shared bath, sleep well and look forward to a gourmet breakfast. Beaches, downtown shops and galleries are all within a short walk of our home. This room is located in the front of our home....
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    01966, Rockport, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 19
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 November 2017
    Lovely apartment, with bonus deck for enjoying a BBQ & wine. Views of the working harbor can be enjoyed right from the bed (which is super-comfy!). Well equipped kitchen, all...
    Reviewed 24 November 2017
    One of the best vacations I've had in years. The owners were charming and attentive but also respectful of my privacy, which is important to me as a writer. The deck was a...
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    About this property
    Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck of this romantic getaway. This property is best described as a “studio plus”, featuring 3 separate rooms (400 sq. ft.): Bedroom with...
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    01930, Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterfront Woodsy 3BR Cottage1 / 12
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Waterfront
    • Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    Our family of 4 (plus two standard poodles) thoroughly enjoyed our stay at this charming spot in the Lanesville section of Gloucester. The sunsets are spectacular, it's very...
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    About this property
    Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage has been hosting travelers and...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Back Beach1 / 15
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2017
    House was wonderful and location perfect. Three generations spending a week making memories and no one was disappointed. Smoke detector battery issue (not something ever...
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    About this property
    Cozy, bright , and ideally located. Unrestricted view of ocean from back of house and large deck. Walk across to Back Beach, 5 minute walk to Front Beach and Main Street downtown. Large fenced yard across from ocean. Beautiful sunrises and sunsets. Train Station 1/2 mile down Granite Street for a...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Dragonfly1 / 7
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
    • Grill
    • Private Garden
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2016
    A big, comfortable home, surrounded by woods, a short walk to the ocean, and a short ride to downtown Gloucester or Rocky Neck. A beautiful, well appointed place. Home for a...
    Reviewed 30 August 2016
    The Dragonfly is a great place to stay for a big group! It is a beautiful home, with so much character and is clearly well loved by Patricia, the owner. It is even better than...
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    About this property
    Spacious home located two blocks from Atlantic Ocean and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat in July & August. Large modern fully equipped kitchen with double oven, 5 burner Viking cooktop, dishwasher, washer, dryer. Three...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    La Boheme RETREAT Studio1 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Patio
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 September 2016
    This unit was a great location! It was easy to get to the train to go into Boston as well as to travel to other sites in and around Boston. My daughter and I loved to sit on the...
    Reviewed 27 January 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
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    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a...
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    01930, Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Beachcomber Suite1 / 11
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2017
    Fabulous food was awesome, she even irons the sheets! Highly recommend staying here. The breakfast was delicious.
    Reviewed 19 July 2016
    It was wonderful to be with Stephanie and Jay - their home is beautiful and welcoming. Stephanie's breakfast is not to be missed! I especially enjoyed the outdoor spaces - the...
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    About this property
    Beachcomber Room, at Changing Tides Bed and Breakfast, features a comfortable king sized bed or 2 twin beds, and an ensuite bathroom. This sunny room has 2 sky lights, a ceiling fan, AC, a sitting room with a small refrigerator, and a shared bathroom. Stay includes daily multi-course gourmet...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    About this property
    This spacious seaside apartment offers 2 bedrooms, 2 bathrooms, and living room/kitchen with a sunny ocean view dining/game area within a bay window. At over 800 square feet it is our largest accommodation. You’ll enjoy Gap Cove’s seaside charm, with amenities including free WIFI, DVD player,...
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    01966, Rockport, Cape Ann
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    18th Century Cottage with attached guest suite1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    Reviewed 27 October 2016
    We just completed our first visit here and plan to return to this house. A Very clean, historic home that more than met our expectations. It is off the beaten path with both...
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    About this property
    Down a quaint lane you will find an Artists cottage and guest suite. The smaller of the two buildings contains a private double bed retreat with en suite, cable TV & Wi fi. The Main house boasts a charming loft bedroom with 2 ex-long twin beds. The ceiling of the second floor bathroom is a large...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy Rockport Cottage with Ocean Views1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 August 2016
    This simple seaside cottage is well situated to some lovely views of the coast, including the light houses of Thatcher Island. The cottage itself is well-maintained with a very...
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    About this property
    Walk to the water from this cozy peaceful cottage with ocean views. This bright and cheerful recently updated vintage cottage is just minutes from nearby beaches. Enjoy beautiful sunrises, birds chirping, and leisurely strolls along the rugged coast. Stunning views of the Thacher’s Island Twin...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Grill
    • Ocean Views
    • Waterfront
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    • Balcony
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated ocean view apartment at the Seaward exudes classic coastal charm. Here you will fully relax while listening to the ocean waves. Lover’s Cove features exposed brick walls, newly conditioned hardwood floors and a king bed. This seaside apartment makes for our most spacious...
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    Location Information
    01966, Rockport, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. One block walk to Good Harbor Beach and scenic Back Shore. We call your home away from home, “Good Harbor...
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    Location Information
    01930, Gloucester, Cape Ann
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spruce Cottage at The Seaward offers a spectacular ocean view setting and charming accommodations. Spruce Cottage, is a quaint and cozy two bedroom cottage with ocean views & fireplace. It has a private queen bed in one room and two twin beds in the other. The living room has a kitchenette and...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    A Year-Round Vacation Home1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2017
    5 adultsHouse is in a great location.Very uncomfortable beds unfortunately. (In all rooms!) -wished there was a queen bed instead of a double in ocean view room-) there...
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    About this property
    $1750 (off season) - $2,100 (peak season) per week .... Fresh sea breezes keep the inside cool during the summer and a large fireplace in the living room makes this a cozy winter getaway. The home comfortably sleeps five, has a completely furnished kitchen, a dining room, and a masonry fireplace in...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    One Bedroom Loft Apartment B at Cedar Hill Farm B & B1 / 6
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2017
    This was our first stay in a B&B, it did not disappoint! It was very clean, cozy and conveniently located to the town of Essex. Appreciated the breakfast choices, especially...
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    About this property
    We can now offer Apartment B to our options at Cedar Hill Farm B & B. This apartment is identical to Apt. A also located in our lower barn. The bedroom is on second floor with open to living area and cathedral ceiling. 8 Foot sliders open to open pastures, woods and meadows. Guests can enjoy...
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    Location Information
    01929, Essex, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Close to Half Moon Bay1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your morning coffee and breathtaking sun rises on the covered porch, listen to the birds singing before you walk to Half Moon beach for a relaxing day at the ocean. Private entrance, dedicated parking spot on premise, fully equipped kitchen (with fridge, oven, stove, microwave, coffeemaker,...
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    01930, Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lovely 'Blue Heron Cottage' on Annisquam River!1 / 24
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
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    Pet friendly
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    Reviewed 19 July 2017
    We walked to the beach at Good Harbor and enjoyed crossing the sandbar at low tide to Salt Island. Two grocery stores, liquor store were very close. Gloucester had a small...
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    About this property
    Enjoy a peaceful retreat in coastal New England by staying at 'Blue Heron Cottage' - a lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence will...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    You can't get any closer to New England charm than this condo, called Four Winds, located on Tuna Wharf off Bearskin Neck in Rockport, MA. The view looks directly over the water and is truly picturesque. This is a great place for a getaway providing the choice of cooking in or enjoying the many...
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    Location Information
    01966, Rockport, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Trade the stress of daily life for a laid-back retreat on the New England coast when you stay at this charming Rockport vacation rental. Up to 12 guests will enjoy home comforts such as a private washer/dryer and free WiFi, not to mention a beautifully styled interior and a spacious deck with ocean...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Completely renovated 2+ bedroom, 1.25 bath. Second floor unit. Spacious designer kitchen w/ stainless steel appliances. Large Living room and wonderful master bedroom suite. Close to town center, commuter rail, and Singing Beach. 4 minute drive to Singing beach, 20 minute walk (1.2 mile) 2 minute...
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    01944, Manchester-by-the-Sea, Cape Ann
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Ocean Front Cottage on Scenic Long Beach1 / 52
    (6)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    Pet friendly
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    Ocean Front Cottage Directly on the Boardwalk of Scenic Long Beach - Cape Ann, MA Ocean front-row cottage (152 Long Beach) has a 270-degree ocean front view and is the last house facing east on the boardwalk of beautiful & sandy Long Beach. Location allows full views of the twin lighthouses of...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Vintage Home directly on the Annisquam River1 / 12
    (2)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Porch
    • Internet Access
    • DVD Player
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    • Waterfront
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 2014
    We had a great time. A couple things you might find helpful. There is a shower in the basement bathroom. This house is not handicapped friendly. All the bedrooms are upstairs...
    Reviewed 7 July 2013
    House is fully equipped with everything you could possibly need. Views are spectacular. Sleeping arrangements are comfortable
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    About this property
    This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is covered which is great for...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Quaint cozy pre-Revolutionary house with priceless view of picturesque Rockport village and Atlantic Ocean. Located on quiet dead-end lane next to tranquil pond and small town park. Two-minute walk to beach and town's attractive Main street with shops, art galleries and restaurants.The new...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    At the Footbridge entrance to Good Harbor Beach1 / 17
    (2)Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Terrace
    • Wi-Fi
    • Secure Parking
    • Private Garden
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    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2017
    This beachhouse is a dream. Classy beautiful old beachhouse yet super comfy and homey. Plenty of room and different spaces to accommodate a family with a variety of interests...
    Reviewed 25 October 2016
    Great place to spend a week or more with your entire family. Large house with big kitchen and dining room for family dinners. Walk across the bridge to the beach or sit on the...
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    About this property
    At the edge of Good Harbor Beach, one of the very best beaches in all of New England. Good Harbor Beach, less than 1 hour north of Boston, has a fine white sandy bottom, is cleaned daily, beautiful surf. little undertow, incorporates a saltwater creek. Great for children. 1890s 2-storey cottage...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Granite Pier is a traditional Cape Ann home with an unusual history. Built in the mid to late 1800’s, it was part of the Rockport Granite Company housing workmen who mined the nearby quarries. Blending traditional craftsmanship with modern amenities, this home is quintessential New England with...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!1 / 15
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2017
    Loved our stay at Gloucester Harborview Inn . Great location, spotlessly clean and very welcoming . Highly recommend
    Reviewed 16 March 2017
    I had a wonderful stay at this lovely charming bed and breakfast. Location, accommodations and hostess were excellent.Highly recommend!
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    About this property
    Are you looking for a conveniently located affordable place to stay while you enjoy all that Rockport has to offer? Are you traveling with family or friends and would like the privacy of separate rooms? Our top floor guest rooms (2 available) are perfect for travelers on a budget. Clean and...
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    Location Information
    01966, Rockport, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    This large and comfortable vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the ground floor there is living room with plenty...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Back Beach Cottages - Charming house & guest house1 / 17
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2017
    There are two cottages located on the same property. The ocean views are amazing and downtown Rockport is just a short walk away.
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    About this property
    Back Beach Cottages are a unique 2 cottage property with stunning views of the ocean. The location offers the best of both worlds: it's a quiet and relaxing spot for enjoying the beach and also close to downtown Rockport. The homes are steps away from Back Beach, a 5 minute walk to Front Beach and...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sea Mist Cottage1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Reviewed 11 November 2017
    We came to celebrate our 32nd anniversary. We absolutely loved the Seamist cottage. There were did many wonderful details that were put into this place, we couldn't list them...
    Reviewed 14 August 2017
    We were extremely happy with our stay. The cottage was very clean and had an ocean theme through out. Everything we needed was there! Our daughter (14) slept in the loft and...
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    About this property
    Seamist Cottage is located on a private yard in historic downtown Rockport, Massachusetts, a charming seaside community. Short walks to shopping and art galleries on Bearskin Neck, beaches, train station as well as the Shalin Liu Perfomance Center. We, as new owners, welcome inquiries & feedback....
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Beach &  King Street Inn / Beach House Rental1 / 20
    (4)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Wi-Fi
    • Porch
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    Parking was a little tricky and I have to say I was quite concerned when we first arrived. However, Tim was there to greet us and made sure we found appropriate parking for all...
    Reviewed 7 August 2017
    The Beach & King is the perfect vacation home for our four generation family. The house is spacious and beautifully decorated. The front porch is a lovely spot to enjoy...
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    About this property
    Located across from Rockport's Front Beach, Beach & King Beach House is an intimate Cape Ann home located on the North Shore in Massachusetts. Accommodations at our Rockport home offer a picturesque setting with stunning ocean views and a 5-minute stroll to historic Bearskin Neck and the village....
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront vacation rental is a wonderful inviting family vacation home with bountiful space, located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 5 bedrooms/3.5 baths and the ability to comfortably sleep 12 people, this is a house to bring the...
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
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    About this property
    Built in 1750, this charming vacation rental provides lovely views of the Essex Salt Marsh and is centrally located to everything Essex has to offer. Indigo Blue is steps away from downtown Essex, with its numerous restaurants and a wide assortment of antique shops. Indigo Blue is also perfectly...
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    Location Information
    01929, Essex, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    5 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **There is a possibility that construction will ongoing near the property during the summer of 2016** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two separate living spaces as...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 13
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rockport in town private cottage within walking distance to town and all Rockport has to offer: beaches, restaurants, art galleries, shops, Shalin Liu performing arts center, Bearskin neck and the train. *The cottage is 2 floors. On the first floor is a fully equipped kitchen, with a cooler for...
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    01966, Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Located in East Gloucester, Massachusetts wake up in a dramatic furnished waterfront 2 bedroom and one bathroom apartment living at the edge of Gloucester's Inner Harbor. The unit has hardwood floors with an open concept living with cathedral ceilings and windows galore ! Watch the sunset from a...
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    Location Information
    01930, Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Bed & Breakfast is located in the small New England coastal town of Essex, MA. on Cape Ann. Historic farmhouse built in 1695 on 18 pristine areas of forest, fields and meadows. First free school in state. Front field used during Revolutionary War for militia training. House completely updated...
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    Location Information
    01929, Essex, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful summer vacation rental cottage, overlooking broad stretches of the Atlantic Ocean and Rockport's Hoop Pole Cove, is a perfect retreat for anyone looking to experience the best of New England. The wraparound porch and expansive yard allow you to fully enjoy Cape Ann's natural beauty....
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    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Enjoy the beauty of Cape Ann at this romantic cottage. Direct ocean front in America's oldest seaport. Immaculate 2 bedroom cottage brings back memories of long ago. At the end of a dirt road, the cottage offers a wrap around porch, rolling green grass, granite steps leading to a flat rocky...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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