We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Manchester-by-the-Sea House Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    R 5 343 Average
    |||
    |||
    R 0R 12 000+
    Suitability
    More filters
    Don't let other travellers get your favourite Manchester-by-the-Sea area holiday rental. You're so close to securing your perfect getaway. Book today.
    107 Matching Rentals in the Manchester-by-the-Sea AreaView all 176 rentals
    Sort by:
    Default
    Manchester-by-the-Sea
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Manchester-by-the-Sea
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Manchester-by-the-Sea
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Manchester-by-the-Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Grill
    • Patio
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cottage was built in the 1920s and recently renovated. At the end of a long driveway on the back of an old estate, it is very private and yet within 10 minutes walk of Singing Beach and less than a mile from the town of Manchester. So there is easy access to shops, restaurants, and even...
    View all property information
    Location Information
    01944, Manchester-by-the-Sea, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    The following rentals are within 15 kilometres of Manchester-by-the-Sea.
    Back Beach1 / 15
    (2)Excellent
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Waterfront Woodsy 3BR Cottage1 / 12
    (1)Excellent
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Gloucester
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedrooms, 3 Baths (Sleeps 8) beautiful views, steps to private coffins beach Beautiful single family beach cottage, nestled among the pine trees, located on the private side of Wingaersheek Beach, which is well known as one of the most beautiful beaches on the North Shore, with 1.5 miles of pure...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    Rockport
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Beachcomber Suite1 / 11
    (2)Very good
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Save time - get the best Manchester-by-the-Sea rentals sent straight to your email!
    Get the List
    Dragonfly1 / 7
    (2)Excellent
    Gloucester
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
    Make Enquiry
    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set upon Great Neck hill, this antique winterized cottage has a great ambiance and a nice view of the water where the Atlantic meets the mouth of Ipswich River. Spacious and fun for families and small groups, you can walk right down to Pavilion Beach within 10 minutes and access to famed private...
    View all property information
    Location Information
    01938, Ipswich, Massachusetts
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Grill
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Gloucester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    A Year-Round Vacation Home1 / 15
    (1)Very good
    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    Suitability
    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...
    See all reviews
    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...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Vintage Home directly on the Annisquam River1 / 12
    (2)Very good
    Gloucester
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Cable/satellite TV
    • 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
    See all reviews
    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...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Patio
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique beachfront vacation home has been completely remodeled but retains hints of its historical importance; it was the original U.S. base for the first Trans-Atlantic Cable in 1884. Originating in Ireland, the cable went from Nova Scotia to Cape Ann and back to France. Here is an excerpt...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stately Victorian home just above Gloucester’s historic harbor evokes the feel of a gracious bygone era. Elegant and spacious, the home has belonged to the same family since the 1880's and was lovingly renovated to offer modern amenities and comfort. Beachmont has a formal parlor, separate...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Waterfront
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A great vacation starts with a unique destination and a space that suits your needs. This great little cottage promises a unique experience because of it's ambiance and location. A great old-fashioned cottage that is updated for convenience. It overlooks the Little Neck inlet with a great view of...
    View all property information
    Location Information
    01938, Ipswich, Massachusetts
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine a summer of bliss, swimming from the dock at high tide, or from the sandy beach at low tide, when you stay at Annisquam Singing Pines. Or easily paddle to one of the nearby islands or to Wingaersheek Beach for a day in the sand and surf. Annisquam Singing Pines is situated on over an...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Housekeeping Included
    • Terrace
    • Secure Parking
    • Private Garden
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    August 28 thru LABOR DAY, which is Sept 5. 9 DAYS FOR PRICE OF 7!!! in idyllic Island of Little Neck. Check out lower prices in beautiful month of September. Surrounded by water views. Perfect for children. Private beach for Little Neck. A stones throw to Cranes beach and castle. This is a gated...
    View all property information
    Location Information
    01938, Ipswich, Massachusetts
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the ambiance of Victorian Gloucester with all the amenities of the 21st century from this classic period vacation rental home, which is tastefully decorated with the traveler in mind. Enter the house through the front door and enjoy two parlors--one with a large bay window and entertainment...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Enquiry
    Gloucester
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Wi-Fi
    • Waterfront
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your family will love this extraordinary waterfront vacation rental home with spectacular views. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, views abound from almost every light-filled room. The house offers three levels of sophisticated, yet comfortable living space....
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    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...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fabled boulevard and the “Greasy...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Gloucester
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Gloucester vacation experience awaits you in this spacious and versatile vacation home. Bell View can accommodate up to 16 people, making it the perfect getaway for family reunions or vacations with friends. The house was completely refurbished and refreshed in 2017. Inside, a one-of-a-kind...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
    Make Enquiry
    Cher Ami: West Gloucester condo just 0.3 mi to Cressy's Beach.1 / 17
    (1)Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2016
    everything about this place was A+ ,the owners ,the apartment ,the location,the scenery,everything was awesome
    See all reviews
    About this property
    Welcome, cher ami ('dear friend'), to this gleaming second-floor vacation rental. Cher Ami is available as a summer rental and an off-season rental. Cher Ami is a spacious and sunny apartment, with 2 bedrooms plus an office space, an eat-in kitchen with an island, 2 bedrooms plus an office...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    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...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Captain's Cottage: Traditional setting with a private footbridge to the beach1 / 16
    (1)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2016
    We stayed here for a week and Loved it!! It's soo private and quite the only thing we could hear at night were the crickets and crashing waves of the Atlantic! The Captain's...
    See all reviews
    About this property
    This delightful vacation rental cottage is located on a quiet Rockport lane less than 100 yards from the sands of Cape Hedge Beach. Just cross the lane and walk over the footbridge and you're on the beach! This cozy two bedroom beach house is pine-paneled, in the traditional summer cottage...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Waterfront
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2.5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious sunrises, the views from Wonson...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Balcony
    • Parking
    Suitability
    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...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 13
    Make Enquiry
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Patio
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rockport oceanfront! This sunlit vacation rental home couldn’t be closer to the water, situated on a bluff overlooking Sandy Bay and Pigeon Cove Harbor. Popples Cove House offers everything you could hope for in a vacation getaway – scenic views, location, privacy, comfort and air conditioning....
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Rockport
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious 5 BR vacation rental home is steps from Old Garden Beach as well as a short stroll into the seaside village of Rockport. Make this delightful house your home base for your beach escape this summer. The main level of the home consists of the gracious and architecturally stunning sun...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Rockport
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This inviting family vacation home has bountiful space and is located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 6 bedrooms, 3.5 baths and the ability to comfortably sleep 10 people, this is a house for the extended family to enjoy. This area of Rockport...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful 3 bedroom, 1.5 bath Queen Anne-style vacation rental home is bright and cheery and just waiting for you! Enter the house into the kitchen from the verdant and sizable back yard (or choose one of the other 2 doors). The sunny kitchen has plenty of storage, a gas range, and a small...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Directly on Long Beach Rockport MA1 / 92
    (4)Excellent
    Rockport
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Central Heating
    • Patio
    • Cable/satellite TV
    • Ocean Views
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 July 2017
    The location of the house is absolutely magnificent. 3rd house from the end of the Longbeach road, you have an amazing view of the sea. The house on 3 floor is enough big to...
    See all reviews
    About this property
    Waterfront Home on Beautiful Long Beach on Cape Ann Fully renovated for 2016, this light-filled, three-level beachfront home sits on the seawall above sandy Long Beach. We're at the Rockport end with no second-row cottages behind. Views of the ocean, beach and marsh greet you through large...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Enquiry
    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated home. New to the 2014 season. Great for families. Rent just one town-home or rent the entire town-home w/ friends or family. This listing is for the first floor. Each residence has three bedrooms (two large bedrooms and bedroom/office). Office can be used as a third bedroom....
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore one of America's oldest towns during your stay in this sleek home, featuring an upstairs deck for direct access to the Atlantic's fresh air. Central air conditioning and Netflix streaming capabilities invite visitors to unwind after a day exploring rocky shores and seafood markets. Dive...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Rockport
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Waterfront
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Grill
    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...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Season-June through September- Aug 26 to Sept 9 (2 weeks in a row); Directly on the Atlantic with spectacular ocean views opposite Thatcher’s Island’s Twin Lights. Relax on the wooden deck off the 16 foot sliding glass doors from the living room/dining room. On the right of the house is a...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic 'Gloucester Fisherman at the Wheel' sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets,...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Internet Access
    • Grill
    • Air Conditioning
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Antique colonial offering a large place to spend time with family and friends. With lot's of place to sleep and chat. The location is perfect - just across from Stage Fort Park -- featuring a kids playground, Dog Park, Half-Moon Beach, Farmers Market, Sunday summer concert series, Gloucester Blue...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
    Make Enquiry
    Gloucester
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all is kept cool with central air...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For the adventurer, this home is a short swim away from Good Harbor Beach. Located on the edge of a scenic marsh, you can swim or paddle your rented kayak or SUP over to the beach. Enjoy the day on the sands and then either come back on the tide or cross over the foot bridge and walk home the...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Beverly
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Waterfront
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in a cul de sac and fronting on the Crane River, Afternoon Delight in historic Beverly is the perfect place to watch the river currents glide by. The riverfront wraparound deck offers a blissful place to sit or dine in either sun or shade, thanks to an exterior awning. In the garden, the...
    View all property information
    Location Information
    01915, Beverly, Massachusetts
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Gloucester
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sun when you want it. Shade when you need it. Cool Cove is a beach house vacation rental that has it all! Sitting above Wingaersheek Beach, you will feel like you can see forever, enjoying views of Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, and sandbars. Walk from this...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From its waterfront perch, this 4BR vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectacular, unobstructed views of Sandy Bay. The location of the home is ideal, away from all the hustle of town, but within a 10-15 minute walk to everything you might want,...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Washer
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Labor Day Week- First week in September still AVAILABLE. from 9/2 to 9/9 - Book now ! Unobstructed OCEAN VIEW from every window! 3 BR HOUSE WEEKLY VACATION RENTALS - The Glenellen Cottage Delightful, late 1800's, newly renovated kitchen with 1st & 2nd floor full bathrooms, non obstructed...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Rockport
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the comforts of modern day living while you step back in time in this updated colonial-era vacation rental home. From the moment you turn the brass door knob, which is original to the house, you will feel steeped in history. Filled with light from the large windows throughout, and with 4...
    View all property information
    Location Information
    01966, Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Good Harbor Beach, one of Gloucester's finest stretches of sand, is just a five minute walk from this comfortable ocean-view vacation rental home. Spend the day at the beach where you can swim, soak in the sun, or walk at low tide out to picturesque Salt Island. Prefer to stay at the house? Relax...
    View all property information
    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    1
    List your property
    Owner log in