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Deer Isle Luxury Holiday Homes

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    Travellers to Deer Isle are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    23 Matching Rentals in Deer IsleView all 155 rentals
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Reachview Estate is located on the northeastern portion of the large portion of Deer Isle, gracing the shores of the well known sailing waters of Eggemoggin Reach. Eggemoggin Reach is a breathtakingly picturesque body of water - 10 miles long and 1 mile wide, connecting East Penobscot Bay with...
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    Sunset, Deer Isle 4627
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    About this property
    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...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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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...
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    Stonington, Deer Isle 4681
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to Nanmark (formerly known as the Crow's Nest). This waterview home is perched just above town and has one of Stonington's most spectacular views. This home is one of the most painted and photographed around. (Even gracing the cover of Downeast Magazine a time or two!) Nanmark's location is...
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    Stonington, Deer Isle 04681
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    About this property
    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,...
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    Sunset, Deer Isle 04627
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lighthouse Point Estate1 / 8
    (1)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Over 5000 sq ft exclusive oceanfront estate with gourmet eat-in kitchen with fireplace (subzero appliances, granite countertops, 6 burner Garland Stove, fully stocked with quality items, kitchen desk, dumbwaiter), great room with cathedral ceilings and fireplace, dining area, professional level...
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    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    About this property
    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, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Dalton Cottage1 / 8
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Washer
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    Pet friendly
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    Smoking allowed
    Reviewed 4 October 2015
    Spent two weeks in this wonderful house. Everything was perfect - especially after Michele explained everything to us. Very romantic. Very peaceful. Fantastic sunsets. The...
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    About this property
    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,...
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    Location Information
    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cottage on the Shore rests in one of Deer Isle's most picturesque settings. Rarely does property of this caliber become available for new development. But this newly built home graces family land owned for generations, and is prime real estate. The setting offers lush, wooded privacy,...
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    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Reachable by bridge, Deer Isle is a cluster of small fishing communities located on 24,000 acres with 112 miles of shoreline. With a year-round population of about 3,000 residents, lobstering continues to be the mainstay of the economy, and Stonington, the village on the south end of Deer Isle,...
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    Deer Isle, DownEast and Acadia Maine 046273 4
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, 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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    • Grill
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    Smoking allowed
    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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    About this property
    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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    Reachview Estate1 / 8
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Reachview Estate is located on the northeastern portion of the large portion of Deer Isle, gracing the shores of the well known sailing waters of Eggemoggin Reach. Eggemoggin Reach is a breathtakingly picturesque body of water - 10 miles long and 1 mile wide, connecting East Penobscot Bay with...
    View all property information
    Location Information
    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Sunset, Deer Isle 4627
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Porch
    • Ocean Views
    • Balcony
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pickering House is an old sea captain's house with over 3000 sq feet of relaxing Down East charm. There is ample space, inside and out, which offers the perfect setting for larger families and group gatherings of up to 10. The house itself is situated on a gentle sloping hill across the street...
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    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Stonington, Deer Isle 4681
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New custom-built house on 2+ acres in private, waterfront setting. Three bedrooms; two with queen beds, one with twins. Fully equipped kitchen with KitchenAid stainless appliances and lots of counter space for the cook in the family. Home offers two dining areas: an indoor area and a screened...
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    Deer Isle, DownEast and Acadia Maine 04627
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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