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Holiday Homes in Deer Isle

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    Travellers to Deer Isle are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 104 Rentals in Deer Isle
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    INSMERE - Stonington1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Spacious Shore House Overlooking Penobscot Bay1 / 8
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    CAMPRENE - Stonington1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    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 04627
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    At Peace Downeast is a beautiful oceanfront home in the scenic, quiet, and private Plumb Point neighborhood. Enjoy four acres of forest, a small and sandy pocket beach, deep water dock and a well-built post and beam home in this amazing setting. At Peace Downeast is a two bedroom, two and a half...
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    Sunset, Deer Isle 04627
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Big Yella is a historic ocean view home in Deer Isle Village. This classic home dominates the hillside and enjoys views of Northwest Harbor. The home has a central island location making it easy to head to Stonington or Sedgwick. Big Yella is a six bedroom, three and a half bathroom home. The home...
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    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    SEA CLIFF COTTAGE - Stonington1 / 12
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 1 July 2018
    Wow, coming up the driveway through the forest prepares you for what a gorgeous home, views and incredible property surrounding the cottage. The cottage was perfect, we loved it...
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    About this property
    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 04681
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    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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    Stonington, Deer Isle 04681
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    About this property
    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 04627
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Muir Point is a superb oceanfront home in Stonington. Enjoy being on forty-five acres of gorgeous forest and oceanfront. This property consists of multiple pocket beaches with sandy bottoms and trail walks through the woods. A beautiful contemporary home graces the middle section of this pristine...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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 04627
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    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 04681
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    STINSON POINT RETREAT - Deer Isle1 / 30
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Reviewed 26 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 04627
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    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 04627
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    FIFIELD POINT GUEST COTTAGE - Stonington1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 13 February 2017
    What a lovely home! Floor-to-vaulted-ceilings-windows light the spacious living areas. Walk across the lawn of this peaceful location to the floating dock.
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    About this property
    Fifield Point Guest House is a bright and clean home with ocean frontage on Burnt Cove in Stonington. Enjoy easy access to the cove from the dock, which makes launching your kayaks quick and easy. The cottage has a convenient location, just a couple miles from Stonington village and less than a...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Ocean Breeze is a classic, well-maintained home in the village of Stonington. The home is nicely situated on a hillside overlooking the bustling waterfront. Enjoy watching lobster men bring in their daily catch and schooners coming in to port from this village locale. Ocean Breeze 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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    GRAY HOUSE - Stonington1 / 14
    (3)Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 3 weeks ago
    Joanne and I loved the peace and quiet. The Lobstermen are very respectful. We would like to come back in the future.However the comments I made to the Island Agency has to be...
    Reviewed 5 October 2017
    We are enjoying our visit at the Grey House. Beautiful setting with the benefit of witnessing a true Maine fishing town. The house is comfortable but can use an update of the...
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    About this property
    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 04681
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Overlooking Northwest Harbor on Deer Isle, this oceanfront estate has 4 bedrooms and 2 full/split bathrooms. The setting for this very private cottage is unparalleled, on more than five acres with over 300 feet of shoreline and expansive gardens. This charming home was built by Richard Myrick as...
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    Sunset, Deer Isle 04627
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    BLACK SWAN - Stonington1 / 29
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Reviewed 18 September 2016
    Perfect base for our Maine travels! In Stonington for a family wedding, a comfortable,sparkling clean home that is well equipped with everything we needed. Perfect private...
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    About this property
    Black Swan is a well-maintained, in-town home with panoramic views of Stonington’s thoroughfare. Enjoy the changing scenery of the working waterfront throughout the day, as lobster boats, sailboats, schooners and other vessels work the waterways. Black Swan is a ranch style home with all the living...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Beauty abounds at this amazing property, with 28 acres and 500 ft of shore frontage on the famous sailing lanes of Eggemoggin Reach. It has spectacular views looking across the waters to Naskeag Pt and the multiple islands in between. These popular sailing lanes are traversed by a variety of...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Meander down to the impressive 730 feet of shorefrontage on this beautifully situated cottage resting on 8.5 private, wooded acres. This charming home boast cathedral, beamed ceiling with massive brick fireplace reaching to its lofty heights. The open livingroom, dining room and kitchen are...
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    Stonington, Deer Isle 4627
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Sweet Grass Cove Cottage is located down a long private drive to the shore. Surrounded by woods and wildlife on one side and ocean front on the other. A very quiet and peacefully spot for the family or couple looking to get away from it all. Enjoy the ocean breeze from the large deck or take a walk...
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    Sunset, Deer Isle 04627
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    About this property
    Spectacular modern home, all natural wood, original features and paint, designed by Emily Muir. Floor to ceiling windows on two sides, with front deck overhanging waters of Crockett Cove. Stunning views of Rabbit Island, the 'Falls ' tidal rapids and Penobscot Bay provide ever-changing scenery....
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    Stonington, Deer Isle 4681
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Cottage on the Shore rests in one of Deer Isle's most picturesque settings on family land owned for generations. The setting offers lush, wooded privacy, an outstanding beachfront, and views across the bay to spruce clad islands and the hills of Camden in the distance. It would be near impossible...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    This wonderful family home boast a PRIME oceanfront setting. Located on a nearly 100 acre seaside parcel on Buckmaster Neck on Spruce Harbor, the Main House overlooks the Deer Isle Thoroughfare, multiple islands, including Sheep and Saddleback Island, as well as many other nearby islands. It has a...
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    Stonington, Deer Isle 4681
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Wonderful vacation hide-away home sitting oceanside in lush wooded setting at edge of Southeast Harbor. Beautiful shorefront and outstanding views over the bay. All on one level this Emily Muir designed cottage has a cathedral beamed ceiling in the living and dining areas, an efficient galley...
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    Stonington, Deer Isle 4681
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    About this property
    Stunning newly built contemporary on Web Cove, just a 5-10 minutes ride in to downtown Stonington. Beautiful, peaceful and private setting. Home is a fabulously unique design, with soaring ceilings, catwalks, skylights -and much more. Quality amenities and decor throughout. The floor plan is open...
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    Stonington, Deer Isle 4681
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Contemporary Emily Muir designed house with 300 feet of granite shoreline in the seclusion of 8 acres of woods and boulders, adjacent to Nature Conservancy land with walking trails. Spectacular western views from large living/dining room with floor to ceiling windows and beamed and wooded walls and...
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    Stonington, Deer Isle 4681
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Privately situated cottage on 3+ acres with steps leading down to the 300 feet of shore frontage and beach. Excellent views of water and surrounding spruce woods. Cathedral ceilings add to the light, open and cheery feel. Enjoy the well equipped kitchen, with fresh herb & flower gardens growning...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    With outstanding beachfront on East Penobscot Bay, this striking, privately situated, 8.7 acre, natural-styled contemporary house faces due west and enjoys excellent views across the bay to Camden Hills in the distance - including breathtaking sunsets. Attractive landscaping surrounds the home, and...
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    Sunset, Deer Isle 04627
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Quiet, secluded large family waterfront home nestled in the trees. Beautifully built in stone and wood. Bright and sunny. Ideal Maine get-away. Perfect for kayak excursions, and quiet relaxed time, but also close to Stonington. - Wonderful spaces to relax at the home: cosy indoor window seat area,...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    This lovely cottage was designed by artist Emily Muir, utilizing a unique combination of rustic and contemporary style and color. It sits high overlooking Crockett Cove, with spruce trees shading the open deck running along the waterside of the home. Large windows take in this private and quiet...
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    Stonington, Deer Isle 4681
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Waterfront! Secluded. Premier oceanfront 6 acre, 5 story post & beam estate with soaring beamed ceilings and westerly views overlooking Penobscot Bay and across to the mountains of Camden. SUNDAY TO SUNDAY RENTAL Over 5000 sq ft exclusive oceanfront estate with gourmet eat-in kitchen with fireplace...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Heron Watch is a gorgeous privately situated waterfront home positioned at the head of a tidal cove featuring expansive views over the cove that opens into to Mount Desert Island. With over 2 1/2 acres, the ranch-style home sits on well-manicured lawns surrounded by woods to explore. This is a two...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    A lovely family home on Greenlaw Cove. Nice open floor plan, with pine walls adding warmth and coziness. Sliding glass door open to wrap-around deck, all overlooking Greenlaw Cove. Two nice bedrooms (queen and full) and 2 bathrooms are on the main floor. Spacious upper floor for added sleeping...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Outstanding property! New post and beam cottage sits on 6 acres of woodland, nestled in amongst trees with ocean views. When you visit Heron Cove Cottage you will have that warm and cozy feeling of downeast Maine. A great spot to launch kayaks, watch wildlife, and listen to birds singing as the...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Located in one of the most beautiful areas of Deer Isle, Rugosa Way is nestled on 2+ acres of landscaped grounds with wooden stairs gently descending to the 220 ft of deep water, pebble beach, oceanfront. The shore is perfectly suitable for swimming, kayaking or canoeing. This quality-crafted cedar...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Owner Direct: For this property, please email Barbara at barbwescott**********, or call *******-0150. Harbor Heights Cottage is a charming and lovingly remodeled victorian located on Stonington Harbor, in the areas most prime kayaking waters. It is just around the corner from the town center of the...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    Privately situated at the end of a winding wooded lane, The Cottage is nestled at the edge of 100 acre wooded setting, along the granite ledges of Spruce Harbor. Floor to ceiling multi-paned windows adorn the south side of the home, opening to expansive ocean views. Skylights shimmer light...
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    Stonington, Deer Isle 4681
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Park Place is a cozy, rustic cabin nestled in private wooded setting. It is located on a peaceful cove that opens to Southwest Harbor and multiple islands, coves, inlets and ample areas to explore. It is centrally situated between both Deer Isle Village and the downtown Stonington area, offering...
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    Sunset, Deer Isle 04627
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterhouse Cottage is a quality designed, cedar shingled cottage, located in a private wooded setting of Potato Cove on the much-desired shores of Eggemoggin Reach. It boast sweeping views across the Reach, looking west to the Deer Isle Bridge, and east towards Benjamin River. The interior...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lachman Cottage is one of the treasured natural-styled contemporary homes designed by revered artist Emily Muir. True to her style, Lachman Cottage is built in union with the natural surroundings. Situated securely on rocky outcrops above the water, it has a 'nest-like' vantage above the scenic...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    This adorable, well kept/immaculate camp exudes old charm. It sits at the waters edge on Greenlaw Cove, in a peacefull and sereen setting. The gabled ceilings, sun room and open plan allow for a spacious feel. A deck runs along the front of the camp, allowing for relaxation in the open sun right...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Oceanville Retreat is located at the end of a 7/10 mile long drive to a granite lined shorefront, tucked away in a quiet and private setting. Situated only 100 feet from the sea with southern exposure, it has direct views of Isle au Haut from the spacious deck, which runs along the entire waterside...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Dorsey Cottage is situated on a quiet cove that is just off the popular sailing lanes of Eggemoggin Reach (a mile wide body of water separating Deer Isle from the mainland). This picturesque cove wraps around two sides of the home, and provides for more expanded views northeast looking out across...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, 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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    Natural styled cottage only 50 ft from beautiful, bold, deep water ocean. The location is completely private and quiet. The views are stunning. Perfect for the true adventurer who doesn`t mind roughing it a bit. There is no electricity and no phone. Gas appliances and normal bath and shower fed...
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    Stonington, Deer Isle 4681
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Wolfhound Cottage, a beautifully built post & beam cottage, sits at the end of a dirt road surrounded by moss-covered boulders and tall, wind blown, spruce trees - the classic Maine forest. A 110 acre, nature preserve is right next door providing ample walking trails. A short stroll (about 200...
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    Stonington, Deer Isle 4681
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Relax, literally cove side, perched above majestic granite retaining walls providing for elevated and close up views of Stonington Harbor. Enjoy these close at hand views and interesting harbor activities - just outside your windows! Gaze to distant Isle au Haut, channel islands, kayakers and...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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