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Deer Isle Holiday Rentals

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    Travellers to Deer Isle are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    2 Bedrooms, Sleeps 6Quick View
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    1 Bedroom, Sleeps 3Quick View
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    3 Bedrooms, Sleeps 5Quick View
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    About this property
    Get back to the basics in this lovely, rustic cottage located just feet down the road from beautiful Sand Beach in Stonington. This one-bedroom cottage is small and simple. Enjoy views of the pasture and cove while relaxing on the covered porch. The porch is equipped with a small table and three...
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    Stonington, Deer Isle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, Sleeps 6Quick View
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    Kramer Cottage is perched on a hill and overlooks Long Cove and beyond to Sawyers Island. The property extends to the water where guests can access the gravely beach area by a set of stairs. Enjoy beautiful water frontage as well as access to the family’s private island, Sawyer’s Island, when...
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    Deer Isle, DownEast and Acadia Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    Changing Tides is a inspiring, secluded oceanfront log cabin in Deer Isle. Enjoy being off-the-beaten path as you watch the tides roll in and out, while soaking in all the beauty and peace our little island has to offer. Changing Tides has a grandfathered building site sitting just above the...
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    Deer Isle, DownEast and Acadia Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 8Quick View
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    Osprey Point Retreat is a beautiful, contemporary home in a relaxing, quiet neighborhood in scenic Deer Isle. Enjoy watching the tides come and go from the wrap-around deck or from many rooms in the house. Osprey Point Retreat is spacious and well equipped. The home is pet- and child-friendly,...
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    Deer Isle, DownEast and Acadia Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 5Quick View
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    Take a step back in to time when visiting this classic Victorian, poised high above the picturesque sights of Stonington’s thoroughfare. Grandpa’s Cottage eastern views of open ocean makes for a spectacular sunrise over the bay and an otherwise peaceful setting to watch the tides change. Grandpa’s...
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    Stonington, Deer Isle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, Sleeps 4Quick View
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    Tide Watcher 2 is a well-decorated apartment on West Main Street in Stonington’s seaside village. Enjoy watching the boats and tides come and go from this bright and airy in-town location. Tide Watcher 2 is a two bedroom, one bathroom apartment. The space has an attractive backyard as well as two...
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    Stonington, Deer Isle
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    Cove's End is a gorgeous, cove-side home on a private drive overlooking quiet Long Cove. Cove's End is beautifully furnished and pleasantly situated with long views of the cove. See clam diggers working, watch birds come and go in the cove, or paddle around in one of the four kayaks available for...
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    Deer Isle, DownEast and Acadia Maine 120
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    Pleasant View is a bright and cheery New Englander style house located on a quiet cul-de-sac in the heart of Stonington village. Enjoy views of Stonington harbor, a clean and fresh space with all the conveniences of home and an artist/writing retreat with views of the thoroughfare and islands...
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    Stonington, Deer Isle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cottage at Lily Pond is a secluded family retreat just outside of Deer Isle Village. Enjoy access to Deer Isle's lovely Lily Pond while relaxing in a private location. Cottage at Lily Pond is newly constructed and enjoys great acreage for guests whom like to hike, bike, bird watch or just enjoy a...
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    Deer Isle, DownEast and Acadia Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    Cabin on Pressey Cove is a simple one room cabin in a fun oceanfront setting. Enjoy tidal ocean frontage, which offers beach at low tide and beautiful ocean water at high tide. Cabin on Pressey Cove has the basic needs that one would want but not too many extra frills. The cabin enjoys a private...
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    Sunset, Deer Isle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Allen Cove Cottage is a bright, airy home located off West Main Street in Stonington. Enjoy views of Allen Cove and Moose Island from this convenient, in-town location which leaves you just a short walk away from the village's restaurants, galleries and novelty shops. Watch pleasure boaters,...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Morning Mist Cottage is a delightful in-town home with views of Stonington Harbor and the Deer Isle thoroughfare. The cottage is well maintained and beautifully decorated with a great mix of modern and antique pieces, exuding Maine charm. Morning Mist Cottage is located within walking distance to...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8Quick View
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    Warren Point Cottages are a trio of cabins that come together to create one enchanted lodging. The cottages were built in the 1960s and have been lovingly maintained by one family for years. The property consists of seven acres of woods and ocean frontage. A kayak launch site, a tent platform on...
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    Deer Isle, DownEast and Acadia Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Bay Dream is a beautiful home in the village of Stonington. Bay Dream sits high on top of Granite Street, overlooking Stonington's harbor and the islands beyond. Bay Dream is just steps from many of Stonington's restaurants, galleries, and novelty shops. Bay Dream is a three bedroom, two bath home....
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    Stonington, Deer Isle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    McNamara is a marvelous home on a beautifully landscaped, tidal oceanfront setting in Deer Isle. Enjoy one-level living in this cozy ranch nestled along the shore of Greenlaw Cove. The home has a great amount of natural light that makes the space very warm and inviting. McNamara has two bedrooms...
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    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    Lupine Ledge is a classic home located on desirable Indian Point road in Stonington. Enjoy being within walking distance of the villages restaurants, galleries and novelty shops. Take a day trip to Isle au Haut or just kick back and relax as you enjoy being on island time. Lupine Ledge is a three...
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    Stonington, Deer Isle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 7Quick View
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    • DVD Player
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    Welcome to Picnic Cove. This contemporary home is located in the center of the desirable Merchants Point. Enjoy beautiful views of Long Cove, while vacationing in this private home in Deer Isle. Sunbathe on the wrap around deck, relax away from the pests in the screened porch, take a swim from the...
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    Deer Isle, DownEast and Acadia Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    Very good of 5 bubbles
    Reviewed 6 November 2016
    We stayed here for 3 nights this past spring on our mini trip to Stonington. The location is very convenient and the views are amazing. This is a top of the line rental with...
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    Fisherman’s Loft is a bright and newly remodeled apartment located above the Fisherman’s Friend Restaurant in Stonington. Enjoy a unique prospective on Stonington village and panoramic views of the thoroughfare from almost any window. Fisherman’s Loft is two bedrooms and two bathrooms and is...
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    Stonington, Deer Isle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pretty Penny is a beautiful home located just on the outskirts of Stonington Village. Delight in the sunny, southwest exposures of Penobscot Bay and beyond to Isle au Haut. There are numerous unique features that make Pretty Penny a great place to relax. Enjoy gorgeous weather on the deck, in the...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, Sleeps 7Quick View
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    Welcome to Fuchs Cottage. This gracious Victorian home, on a secluded, six-acre hillside in Stonington, enjoys views of the Deer Isle Thorofare and the islands of the Western Bay beyond. Take a walk along the path to the shore, go for a stroll through Stonington village where you'll find excellent...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    1 Review
    4 Bedrooms, Sleeps 8Quick View
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    Excellent of 5 bubbles
    Reviewed 25 July 2016
    We stayed in this amazing property in July for 7 nights and it was perfect for our family of 8 (including 2 children). Honestly, the photos don't do this property justice. The...
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    Stinson Point Retreat is a luxurious, oceanfront property located just feet from Barred Island Preserve in a wonderfully quiet and serene setting. Enjoy beachcombing, swimming, boating, hiking and even biking from this picturesque location in Deer Isle. Stinson Point Retreat has a desirable,...
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    Sunset, Deer Isle
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    222 Dunham Point is a newly constructed home with three bedrooms, two bathroom in the quiet Dunham Point section of Deer Isle. Enjoy hardwood flooring, modern and comfortable furnishings, and all the conveniences of home. Views of the Penobscot Bay just across the road can be enjoyed from the...
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    Sunset, Deer Isle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, Sleeps 6Quick View
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    Welcome to the Seabreeze House, a five-bedroom house divided into two separate living quarters. Enjoy the views of Stonington Harbor from this in-town home. The Seabreeze House is conveniently located on North Seabreeze Avenue and is just steps from the village of Stonington and The Isle Au Haut...
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    Stonington, Deer Isle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Bonny Briar is a three-bedroom, waterfront home on beautiful Dunham Point Road in Deer Isle. Enjoy being off the beaten path in this recently renovated home. Hardwood floors, granite counter-tops and new appliances; are just a few of the features that make this home a dream vacation spot. A Bonny...
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    Sunset, Deer Isle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Welcome to Apple Island Cottage. Enjoy new construction, top of the line furnishings and a glorious tidal oceanfront setting in this two-bedroom cottage on Fish Creek road in Deer Isle. Apple Island Cottage is wonderfully equipped for any person or family. The cottage is all on one floor with the...
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    Deer Isle, DownEast and Acadia Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Stonington Harbor Condo is a bright and airy third-floor condo with panoramic views of Stonington Harbor and some of the islands beyond. The condo is conveniently located within the hustle and bustle of town, but elevated high above Main Street to allow for optimal views and privacy. Housed within...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    West Harbor Nest is an oceanfront apartment located on West Main Street in the village of Stonington. Enjoy views of Stonington's working waterfront from the kitchen and one of the bedrooms in this little nest. You'll also have the convenience of being in-town, among all of the schooners,...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Welcome to Hattie's Cottage. This bright, classic home on Indian Point Road, overlooks the Deer Island Thorofare and the islands beyond. Hattie's is just a short walk to the village of Stonington and the Lobster Co-Op were you can grab lobster fresh off the boat. Hattie's Cottage is a two bedroom,...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Butler Cottage is a treasured summer cottage, located on the water edge of Hatch Cove, in the beautiful Oceanville section of Stonington. With the ocean as a front yard, there is never a lack of breathtaking scenery, whether it is the working or pleasure boats on the water, the sun rising in...
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    Stonington, Deer Isle
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Water’s Edge is a classic farmhouse overlooking the island of Stonington – the home has a unique position at the end of Deer Isle as you pass over to Stonington. Water's Edge has a couple hundred feet of shore frontage which makes it great for kayaking or other water activities. Water’s Edge is a...
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    Stonington, Deer Isle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sam's Cottage is a cherished family home located on the scenic Indian Point Road in Stonington. With sweeping views of the Deer Isle Thorofare, vacationers are able to watch picturesque schooners, lobster vessels and pleasure boaters come and go. Enjoy being a short walk from the villages and many...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Piscean Path is an adorable oceanfront cottage nestled on the shore of Stonington’s quaint seaside village. Enjoy the changing scenery of the harbor - from the hustle and bustle of the lobster boat fleet to the various schooners that come to Stonington to port. The harbor is always changing which...
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    Stonington, Deer Isle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Sunset House is a classic home conveniently located in the center of the island. The home is sitting on four acres of field and wood and has a large, grassy backyard and a great screened in porch. Sunset House is a three bedroom, one bathroom cape. The first floor of the home has a comfortable...
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    Sunset, Deer Isle
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    • Private Garden
    • Satellite TV
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    Charming and romantic carriage house located among gardens and woods in the village of Stonington. Enjoy morning coffee on either of the two decks. Walk to the beach, theater, restaurants, shops and the harbor. Kitchen utensils, linens and towels included. Canoe available for your use on...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Tide Watcher 1 is a handicapped-accessible apartment in Stonington’s picturesque village. Watch the boats and the tides come and go from this nicely equipped seaside efficiency apartment. The apartment has tile floors, many new and contemporary furnishings as well as a convenient in-town location....
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    Stonington, Deer Isle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sea Cliff Cottage is a delightful cottage perched high above the ocean's edge. Watch the sail boats, lobster vessels, and variety of pleasure boats go about the bay from your perch way above. Sea Cliff is privately located and is comfortably furnished. Enjoy one-level living at Sea Cliff Cottage....
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    Stonington, Deer Isle
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Welcome to The Coffee Loft, a stylish compact apartment in the quaint village of Stonington. Enjoy being amidst the restaurants, shops and galleries that the town has to offer. The Coffee Loft is located above 44 North Café, Stonington’s outlet for small batch, fair trade, organic coffee as well as...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Blue Arches is an oceanfront contemporary home privately situated in Stonington on beautiful Deer Isle, Maine. A haven of peace and quiet with unique architectural features, Blue Arches presents hardwood cherry flooring, built-in cabinetry, conservatory dining and a fire-placed living room with...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 3Quick View
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    The Burnt Cove Loft is a lovely one-bedroom apartment overlooking scenic Burnt Cove. This busy little cove is home to many pleasure boats as well as working lobster vessels. Across the cove, you can watch the lobstermen unload their daily catch. Just across the road, there is easy access to the...
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    Stonington, Deer Isle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    The Gray House is located on Fifield Point on beautiful and bustling Burnt Cove. Perched just feet away from the ocean, you will have easy access to Penobscot Bay and the islands. The house has a ramp and float, which is used by a number of local lobstermen and pleasure boaters but you're welcome...
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    Stonington, Deer Isle
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cove View Apartment is located on the hillside, overlooking busy Allen Cove in Stonington. You'll have a birds eye view of Moose Island and all the happenings of the marina across the bay. You can enjoy the beauty of the Maine coast from the deck of the apartment. Whether you prefer to lounge in...
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    Location Information
    Stonington, Deer Isle 04681
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Welcome to Becks Camp – this treasured family cottage overlooks Pressey Cove and Penobscot Bay. If you are thinking about a vacation in Mid-Coast Maine then this property is a great one. A nice yard, a wrap around deck with many comfortable furnishings as well as a gas grill and a spacious,...
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    Sunset, Deer Isle
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Insmere is a beautiful in-town home with great views of the harbor and off-street parking. The home is very tastefully decorated and nicely equipped to accommodate travelers. Enjoy being in Stonington’s quaint and scenic village where you are just a short stroll to The Opera House for an evening...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 5Quick View
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    Ocean Boulevard is a beautiful contemporary home with dramatic views of Stonington’s thorofare. The home's unique position gives you the distant sights of three light houses and views of Isle au Haut and many islands in between. The home's elevation provides western exposure for phenomenal sunsets....
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    Location Information
    Stonington, Deer Isle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Rockmere is a classic home nicely perched just above the high tide line in the desirable Sand Beach section of Stonington. Enjoy superb water frontage in this rustic and charming seaside cottage. Rockmere is located just a mile from the village of Stonington and only a short walk to the popular...
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    Stonington, Deer Isle
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 5
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    The Half House is a quintessential Maine summer cottage located in the desirable Sand Beach section of Stonington. Enjoy dramatic, elevated views of the Penobscot Bay from this beautiful seaside setting. Half House has western exposure so sunsets from this location are some of the best around. The...
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    Stonington, Deer Isle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8Quick View
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    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    190 Davis Farm Road is a wonderful ensemble of oceanfront retreats at the end of a dead end road in a private, picturesque seaside setting. This lovely family compound includes a main house, a boat house with apartment, a seaside cottage, and a media room above the homeowners private wood shop. 190...
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    Location Information
    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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