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Holiday Rentals near Breakwater Vineyards

35 Ash Point Dr, Owls Head, Maine 04854-3509
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    Don't let other travellers get your favourite Owls Head area holiday rental. You're so close to securing your perfect getaway. Book today.
    31 Matching Rentals in the Owls Head AreaView all 34 rentals
    Luxury Oceanfront Home1 / 24
    (1)Excellent
    Owls Head
    0.8 kilometres from Breakwater Vineyards
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Owls Head
    2.8 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Owls Head
    1.7 kilometres from Breakwater Vineyards
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Owls Head
    2.7 kilometres from Breakwater Vineyards
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Ocean Views
    • Waterfront
    • DVD Player
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Kingdom is a quintessential Maine oceanfront rental cottage located on Ginn Point in Owls Head. Located at the end of a shoreline road this property is surrounded by water on three sides. There is a large yard with pine trees in the front of the house and a charming deck and gardens in the...
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    Location Information
    Owls Head, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Owls Head
    2.8 kilometres from Breakwater Vineyards
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Washer
    • DVD Player
    • Patio
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Every muscle in your body relaxes when you pull into the circular drive at Schooner View. This quintessential Maine vacation rental property has 150 feet of ocean frontage with private beach access and a rolling grassy lawn, just perfect for enjoying the incredible view. Located about 12 miles...
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    Owls Head, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Harcliff-Oceanfront property on Penobscot Bay1 / 14
    (4)Excellent
    Owls Head
    4.0 kilometres from Breakwater Vineyards
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Terrace
    • Waterfront
    • Parking
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harcliff is a large (6 bedroom) summer home located at the end of a quiet town road where local lobster fishermen can be seen hauling their traps. The large front and back lawns allow room for family activities.It is not however suitable for very large groups or weddings. A long pier and rowboat...
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    Owls Head, Mid Coast Maine
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    Owls Head
    3.9 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Travel down a quiet, winding lane that hugs the shore. Turn left onto a gravel road and open the gate. Follow the tree-lined private drive, you know the kind…the one with well-worn paths on each side of a grassy track. Drive up to a house, so unique it almost defies description. Walk around to the...
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    Owls Head, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 10 kilometres of Owls Head.
    Sensational 5* Apt. in 1862 Sea Captain's House1 / 28
    (13)Excellent
    Rockland
    4.8 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Waterfront
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2017
    Had a wonderful stay at this charming place. Cathy and George were amazing hosts that pointed us in many directions to see what we could in the short time we had. We had...
    Reviewed 9 November 2015
    6 friends and I took a get-a-way from husbands and kids for 2 nights here and had the most wonderful time staying here. Everything was very clean and anything we could have...
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    About this property
    Sensational 5-Star Second Floor Apartment in Historic 1862 Sea Captain's House. Watch the harbor activity and the famous windjammers sailing in & out. Views over two lighthouses, the unique Rockland breakwater and the outlying islands. Revel in English & American antiques, and original works of...
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    Rockland, Mid Coast Maine
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Spacious lake house with dock and sandy beach1 / 24
    (1)Excellent
    Rockland
    7.6 kilometres from Breakwater Vineyards
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2017
    The spacious Maine home offers the comforts of home close to nature. Driving over to the coast for daily excursions mixes it up.
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    About this property
    Situated on the shores of pristine and private Crawford Pond, The Lake House is the ultimate for a freshwater get-away. We like it because it is family friendly with comfortable and usable outdoor spaces ranging from a sandy approach to the lake, a dock, kayaks and shaded deck space. Spend the day...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Classic Maine waterfront cottage on stunning Crescent Beach1 / 21
    (2)Average
    Rockland
    2.5 kilometres from Breakwater Vineyards
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2016
    I visited in the fall when the foliage was beautiful. The property is right on the water with incredible views of the ocean and nearby islands. Quiet, secluded neighborhood...
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    About this property
    This seasonal cottage, also known as Crockett`s Cottage, sits on a parcel of land just 25 feet from the water`s edge. Like all proper oceanfront summer cottages, it is oriented towards the water, with beautiful views of the beach and the open ocean from almost every room. A nicely landscaped lawn...
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    Location Information
    Rockland, Mid Coast Maine
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Luxury 5* Apartment in 1862 Sea Captain's House1 / 16
    (10)Excellent
    Rockland
    4.8 kilometres from Breakwater Vineyards
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Parking
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    Our family of five adults was very comfortable here. Well equipped kitchen. Lovely old house. Lots of beautiful prints and artwork to admire. Wonderful hosts!
    Reviewed 18 September 2016
    We spent a week in the downstairs apartment of the Sea Captain's House and had a wonderful time. Cathy and George are such fun and full of information about the area. The house...
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    About this property
    Luxury ground floor apartment in the 1862 Captain Zadoc F. Brewster House perched high above stunning Rockland Harbor. Beautifully furnished with English and American antiques, and original works of art. Dine off fine English china. Enjoy lovely French fabrics & handmade quilts. Elegant and...
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    Rockland, Mid Coast Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rockland
    2.9 kilometres from Breakwater Vineyards
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Garden
    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Heart of downtown home 3 blocks from festivals, boardwalk, restaurants, movies, gelato. Walk to everything! Beautifully decorated, the house features a sunroom, a baby grand piano, large bedrooms, 2 bathrooms, and raised gardens. Access to a shed on property. Two parking spaces available off street...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Rockland
    4.6 kilometres from Breakwater Vineyards
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Homeport is aptly named — this stunning house is truly a home away from home. Situated on the shores of the Weskeag, a beautiful salt waterway, Homeport is nestled in woods offering peace and quiet and privacy. The house is situated on over 2 acres with 350 feet of water front — watch wildlife from...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Marshall Point retreat in coveted Port Clyde1 / 12
    (2)Very good
    Rockland
    6.9 kilometres from Breakwater Vineyards
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    The view from Little White Caps is lovely, over the bay with a sunrise in the morning and lobster boats checking their traps. It was warm enough to keep the windows open at...
    Reviewed 9 August 2017
    The location is wonderful. Easy stroll into town or to the lighthouse. The view from the deck, bedroom and living area is gorgeous. There is a nice backyard area. Port Clyde is...
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    About this property
    White Caps Guest House, sits on historic and beloved Marshall Point Road in Port Clyde – As part of a family compound, it overlooks both Muscongus and Penobscot Bay and provides stunning views of the islands, like Monhegan, that dot the horizon. Cherished by family for years, White Caps and Little...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Rockland
    2.7 kilometres from Breakwater Vineyards
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SummerMaine is privileged to offer Rockledge, one of our premier ocean front properties. Rockledge is the culmination of years of careful planning and design by the owners who have been visiting the Midcoast area for years. This stunning property leaves little, if anything, to be desired with...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Plot your next break at Prosehaven1 / 24
    (3)Very good
    Rockland
    3.0 kilometres from Breakwater Vineyards
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Shared Garden
    • Patio
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 November 2016
    The rental portion of this Rockland ME property is entirely private and self-sufficient, it's beautifully furnished, with a terrific kitchen, living room, two upstairs rooms...
    Reviewed 11 December 2015
    Great location in quiet neighborhood, within easy walking distance to all that downtown Rockland has to offer - good restaurants, art galleries, unique shops, the Farnsworth...
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    About this property
    This writer’s 1803 home in lovely Rockland neighborhood is a leisurely 10-minute walk to downtown and the waterfront. Thoughtful renovations have given the rooms renewed life, with fresh paint on the walls and floors, cottaged furniture, and new beds with crisp linens. The charming space offers a...
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    Rockland, Mid Coast Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Rockland
    2.1 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location/Grounds: Montgomery Cottage is located in the historic and artful city of Rockland in a quiet neighborhood down the block from the harbor, a park, the Coastal Children's Museum, and the Sail Power and Steam Museum. It is six blocks to the galleries, shops, and restaurants on Main Street....
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    Rockland, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Maple Street1 / 12
    (4)Excellent
    Rockland
    3.5 kilometres from Breakwater Vineyards
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2015
    We were a little nervous about sending payment in full to an individual (instead of a company) but Steve was more than happy to answer questions and reassuring about that. The...
    Reviewed 15 September 2014
    We ( two adults and a kid) spent a week in this apartment and were very happy with the accommodations. The place is very well maintained and looks as nice as in the pictures.The...
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    About this property
    Phase Two Completed. It just keeps on getting better. This stunning and beautifully furnished two bedroom unit has just been completed. A second floor apartment close to downtown Rockland and in a nice area of town. There is a large living/dining room with cable TV and stereo. This is a...
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    Location Information
    Rockland, Mid Coast Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Rockland
    3.8 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seal Cove is a gorgeous post-and-beam waterfront house with a large lawn sloping down to Wheeler`s Bay. Walk along the shore of Spruce Head Island, watch lobster boats come in after a long day, kayak along the craggy shores of the Maine coast and then return to this stunning house to relax on the...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rockland
    4.2 kilometres from Breakwater Vineyards
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and renew in our spacious clean home with three bedrooms and all new beds! Oceanside 3 Bedroom upscale home steps away from the Atlantic Ocean and Route 1. This Greek Revival home has original expansive gorgeous woodwork installed in 1850! The original wide pine floors and high ceilings with...
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    Rockland, Mid Coast Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Rockland
    5.2 kilometres from Breakwater Vineyards
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Balcony
    • Cable/satellite TV
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    • Waterfront
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique and one of a kind, Tennyson on the Quarry is a Saturday to Saturday vacation rental home located on a magnificent 4.1 acre quarry in Rockland. This scenic 19.5 acre property has direct, private quarry access and the mineral water is great for swimming. In spring 2016 the quarry was emptied...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Sunrise Summit1 / 49
    (1)Excellent
    Rockland
    7.9 kilometres from Breakwater Vineyards
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2017
    This place has perhaps the most spectacular view of any place we have ever stayed, and we travel extensively. Pictures do not do it justice. The home is unique, well...
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    About this property
    ‘Ocean view’ only begins to describe what this one-of-a-kind Maine vacation rental house is about: ‘best view on the coast of Maine’, ‘you can’t help but feel one with the elements’, ‘no need to go anywhere, its all right here’, ‘unimpeded views exceeding 180 degrees:’ Penobscot Bay, Chickawaukee...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Rockland
    3.8 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Executive Family Home. Meticulously restored antique 3 bedroom, 2 bath home with wood floors throughout. Large eat-in kitchen with new appliances, including washer and dryer. First floor has a front porch with antique stone floor and sun room with two sets of double french doors which open onto a...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rockland
    5.2 kilometres from Breakwater Vineyards
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    With a Tempurpedic bed, large bath tub, and cozy living room, any couple will love this sweet apartment. Walking distance to town, The Good Tern Co-op, The Breakwater Lighthouse, Shopping, Grocery Stores, Gas Stations, and The Samoset Resort and Healthclub. You have ocean views from the kitchen and...
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    Rockland, Mid Coast Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Seabreeze Cove Waterfront Cottage1 / 28
    (1)Excellent
    South Thomaston
    3.0 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Waterfront
    • Grill
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2018
    I have stayed at this property a couple of times now and I can't seem to get enough. The house itself is tucked away down an apple-tree lined lane with ocean on all sides, then...
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    About this property
    This warm and charming oceanfront cottage is everything you’ve ever imagined Maine to be. There are sweeping views of Seal Cove from every room, so you’re never without something beautiful to look at. This 3-bedroom home is located on a quiet street with direct access to the water, so you can...
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    South Thomaston, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rockland 'Harborfront' - across from Samoset1 / 21
    (4)Excellent
    Rockland
    5.1 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Waterfront
    • Ocean Views
    • Central Heating
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2017
    This house is handsome, clean and well-equipped to keep you happy for your stay in Rockland, Me. It is centrally located in mid-Maine, and in the number one location for Lobster...
    Reviewed 30 September 2015
    My family and I have spent many summers in Rockland, Maine. Through the years, we've all aged and this time -- there were two 80 year olds on the trip, so we wanted something...
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    About this property
    The Rockland Harbor House is located directly on Rockland Harbor. The house is 2000 sq ft. and has 3 bedrooms with 2 full baths. The house is located on Samoset road just a short walk to the Rockland Breakwater Lighthouse which is located at the end of Samoset Road. The house is conveniently...
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    Location Information
    Rockland, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rockland
    5.9 kilometres from Breakwater Vineyards
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Michelle Lane is a custom-built 3 bedroom, 2.5 bath free standing condo offering the benefits of a hotel or resort with the privacy and comfort of a private residence. The Village at Rockport is newly built neighborhood between the towns of Rockland, Camden and Rockport. This well planned and...
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    Location Information
    Rockland, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Rockland
    1.4 kilometres from Breakwater Vineyards
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Sleeps 4 in 2 bedrooms and 1 sunporch; 1 full bathroom and 1 half bathroom Your peaceful cottage is in the middle of it all — ideal for day trips. Lupine has been renovated beautifully — the downstairs is open-concept with high ceilings, hardwood floors, a large kitchen, breakfast bar, dining area...
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    Location Information
    Rockland, Mid Coast Maine
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Rockland
    3.3 kilometres from Breakwater Vineyards
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leave your car in our driveway and enjoy all Rockland has to offer. Our 1863 two bedroom home is on a quiet residential street just 2 blocks from Rockland's Main Street. Excellent restaurants, waterfront, unique shops, galleries, museums and live performance venues. The space You will love this...
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    Rockland, Mid Coast Maine
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Lobster Landing1 / 35
    (2)Excellent
    South Thomaston
    7.6 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • Central Heating
    • Patio
    • Washer
    • Wi-Fi
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 December 2017
    We loved our time at this home on the ocean. We rented with 2 other couples and the house easily met our needs. Kitchen was well stocked. Chris, the owner responded quickly to...
    Reviewed 7 September 2017
    After finding out our original rental in Owls Head Maine had water damage and We had to find a new home in four days to Fit our family of seven.. I was frantic looking for a...
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    About this property
    Debating between the comfort of a hotel and the thrill of more authentic accommodations? You’ll get the best of both with this desirable oceanfront home! Lobster Landing sits atop half 1private acre located directly on the Atlantic Ocean, offering a lovely Maine oceanfront getaway. The main house...
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    Location Information
    South Thomaston, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rockland
    2.1 kilometres from Breakwater Vineyards
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1868, this lovely 3-bedroom, 2-bath vacation rental house exudes New England culture and charm in southern Rockland. This updated home accommodates up to 8 travelers and sits within a 5-minute drive to the dynamic shops, restaurants, and museums in historic downtown. Enroll in a sailing...
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    Location Information
    Rockland, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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