50 Best Vacation Rentals in Deer Isle - Holiday Lettings - Cabins

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Deer Isle

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122 Vacation rentals

13

Stonington Vacation home rental

Deer Isle / Stonington

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
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 …see more

from $100 / night

$696 - $850 / week

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from $100 / night

10

Vacation home in Sunset

Deer Isle / Sunset

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Ask about children
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. …see more

from $65 / night

$450 - $525 / week

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from $65 / night

12

Stonington Vacation home rental

Deer Isle / Stonington

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Pet friendly
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 Stoni …see more

from $93 / night

$650 - $950 / week

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from $93 / night

(1) Excellent 

11

Vacation home rental

Deer Isle / Stonington

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Ask about children
  • Pet friendly
Camprene is an oceanfront cottage overlooking Stonington’s working waterfront. This precious family cottage is perched on the rugged coast line and gives the feeling that you are on a boat. Camprene has amazing views and is comfortably equipped making this little cottag …see more

from $86 / night

$600 - $950 / week

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from $86 / night

(1) Excellent 

25

Vacation home in Stonington

Deer Isle / Stonington

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Pet friendly
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 Stoningto …see more

from $158 / night

$1100 - $1400 / week

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from $158 / night

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
Newly constructed contemporary on Thompson Cove, opening to the much desired sailing lanes of Eggemoggin Reach. The interior of Grey Ledge is bright and spacious with ocean views from nearly every room in the house. There is a gourmet, fully supplied kitchen, sunny livi …see more

from $229 / night

$1600 - $2995 / week

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from $229 / night

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Waterhouse Cottage is a quality designed, stunning cedar shingle cottage, located in a private wooded setting on the much desired shores of Eggemoggin Reach. It boast sweeping views across the reach, looking west to the grand arch of the Deer Isle Bridge, and easterly …see more

from $215 / night

$1500 - $2600 / week

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from $215 / night

(1) Excellent 

29

Vacation home in Stonington

Deer Isle / Stonington

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
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 s …see more

from $129 / night

$900 - $1350 / week

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from $129 / night

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Ask about pets
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 …see more

from $135 / night

$945 - $1155 / week

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from $135 / night

(1) Excellent 

8

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
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 uppe …see more

from $120 / night

$840 - $1365 / week

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from $120 / night

(1) Very Good 

8

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
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 …see more

from $390 / night

$2730 - $3675 / week

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from $390 / night

19

Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
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 th …see more

from $186 / night

$1300 - $2000 / week

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from $186 / night

8

Stonington Vacation home accommodation

Deer Isle / Stonington

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
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. S …see more

from $154 / night

$1075 - $1260 / week

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from $154 / night

20

Home rental in Deer Isle

DownEast and Acadia Maine / Deer Isle

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Pet friendly
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 …see more

from $186 / night

$1300 - $2000 / week

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from $186 / night

(1) Excellent 

8

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
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 lands …see more

from $353 / night

$2470 - $2625 / week

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from $353 / night

(1) Very Good 

8

Home rental in Deer Isle

DownEast and Acadia Maine / Deer Isle

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
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, dinin …see more

from $203 / night

$1421 - $2310 / week

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from $203 / night

10

Vacation home in Stonington

Deer Isle / Stonington

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
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 al …see more

from $72 / night

$500 - $650 / week

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from $72 / night

(1) Excellent 

29

Sunset Vacation home rental

Deer Isle / Sunset

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
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 Re …see more

from $300 / night

$2100 - $3900 / week

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from $300 / night

18

Deer Isle Vacation farmhouse accommodation

DownEast and Acadia Maine / Deer Isle

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
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 s …see more

from $315 / night

$2200 / week

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from $315 / night

13

Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
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, …see more

from $133 / night

$925 - $1200 / week

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from $133 / night

8

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Ask about pets
Homes-Caldwell Cottage is located at the end of Dow Road, a much desired location centered on Deer Isle and near Deer Isle village. The setting provides for exceptional views across Penobscot Bay and beyond to the hills of Camden, as well as expansive beachfront to exp …see more

from $135 / night

$945 - $1365 / week

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from $135 / night

8

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Ask about children
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 rela …see more

from $95 / night

$660 - $835 / week

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from $95 / night

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
Some of the most picturesque and outstanding qualities that make the Deer Isle area so breathtakingly beautiful are the meandering inlets that reach deep within the island, dotted with spruce clad island and rocky outcroppings. Spruce Shores Cottage sits nearly at the …see more

from $120 / night

$840 - $1155 / week

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from $120 / night

8

Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
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 downto …see more

from $83 / night

$580 - $685 / week

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from $83 / night

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Oak Point Cottage is perfect for people who are equally happy enjoying waterfront views from a comfy chair inside or by walking along the beach itself. Giant windows with built-in seating and skylights make for a sun-soaked living room that is perfect for reading or rel …see more

from $180 / night

$1260 - $2100 / week

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from $180 / night

8

Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This stylish contemporary cottage is nestled within a private wooded setting - and offers complete peace and privacy. Sweeping banks of windows capture the outside beauty, and bring in the shimmering sunlight whispering through the spruce-clad forrest. Lofty ceiling he …see more

from $128 / night

$895 - $1995 / week

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from $128 / night

8

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Ask about children
  • Ask about pets
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 her …see more

from $122 / night

$850 - $1100 / week

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from $122 / night

(1) Good 

8

Home rental in Deer Isle

DownEast and Acadia Maine / Deer Isle

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
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 peaceful spot for the family or couple looking to get away from it all. Queen in master and queen memo …see more

from $120 / night

$835 - $1155 / week

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from $120 / night

8

Vacation home in Stonington

Deer Isle / Stonington

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
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 provi …see more

from $158 / night

$1100 - $1675 / week

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from $158 / night

(1) Very Good 

8

Vacation home rental

DownEast and Acadia Maine / Deer Isle

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This charming, water facing cottage overlooks an impressively beautiful shoreline and ocean vista dotted with islands, and further surrounded by lush, green grasses and woodland. The home is lovingly decorated with a country flair that is warm and inviting. An open fl …see more

from $135 / night

$940 - $1260 / week

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from $135 / night

11

Stonington Vacation cottage rental

Deer Isle / Stonington

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
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 ava …see more

from $90 / night

$550 - $650 / week

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from $90 / night

8

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Alysadel is a Scandinavian styled cottage nestled within pasture and located on Merchants Point, overlooking Southeast Harbor. It exudes a warm, cabin-type feel with wooden floors and gabled, beamed ceilings. It has a nice, open feel, with open shelving between the ki …see more

from $135 / night

$940 - $1365 / week

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from $135 / night

8

Vacation home in Stonington

Deer Isle / Stonington

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Strategically built on granite ledge to capture stunning views over Crockett Cove, this Emily Muir designed house blends rustic warmth and contemporary intrigue in a breathtaking setting. Cathedral beamed ceilings add an airy feel, uniquely colored panels and built-ins …see more

from $136 / night

$950 - $1470 / week

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from $136 / night

8

Vacation home rental

DownEast and Acadia Maine / Deer Isle

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
This house is designed with fun in mind! Located right on a cove this house has private beach access and includes two kayaks. Explore the fantastic views of the house by paddling along the shoreline and out to nearby islands. A bonus game room you wont find anywhere el …see more

from $180 / night

$1260 - $1470 / week

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from $180 / night

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
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 canoein …see more

from $210 / night

$1470 - $2415 / week

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from $210 / night

(2) Excellent 

8

Vacation home in Stonington

Deer Isle / Stonington

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Ask about children
What a view from this charming little house perched directly on the harbor! Dating from 1858, it has all the quaint older charm, with recent renovations cleverly turning this small cottage in to a little showplace. Space is well utilized, and there is plenty of room fo …see more

from $105 / night

$735 - $1155 / week

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from $105 / night

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
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 …see more

from $360 / night

$2520 - $3675 / week

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from $360 / night

12

Vacation home rental

Deer Isle / Stonington

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Ask about children
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. Wheth …see more

from $72 / night

$500 - $750 / week

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from $72 / night

(1) Very Good 

19

Vacation home in Stonington

Deer Isle / Stonington

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
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 an …see more

from $129 / night

$900 - $1100 / week

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from $129 / night

8

Home accommodation in Deer Isle

DownEast and Acadia Maine / Deer Isle

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Ask about children
  • Ask about pets
This adorably simple cottage was built in the 1920s, and still retains much of the original wicker and rattan furniture, hooked rugs, and chintz curtains, and other charming period pieces. Lounge on the Adirondack chairs in front of cottage, taking in spectacular views …see more

from $100 / night

$696 - $850 / week

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from $100 / night

1