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

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460 Vacation rentals

13

Vacation home in Stonington

Deer Isle / Stonington

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $85 / night

$500 - $600 / week

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from $85 / night

20

Vacation home in Stonington

Deer Isle / Stonington

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
Large former captain's home in the village of Stonington. Perfectly situated on the water to take in all of the hustle and bustle of Stonington's Harbor and just steps to the conveniences of Main Street. The Harbor View House is ideal for large families or groups, provi …see more

from $200 / night

$1,300 - $1,900 / week

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from $200 / night

(1) Very Good 

10

Vacation home in Sunset

Deer Isle / Sunset

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Private garden
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 $90 / night

$500 - $550 / week

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from $90 / night

(1) Excellent 

25

Vacation home in Stonington

Deer Isle / Stonington

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $150 / night

$950 - $1,400 / week

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from $150 / night

15

Vacation home in Stonington

Deer Isle / Stonington

3 6 7 nights min

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

from $210 / night

$1,050 - $1,785 / week

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from $210 / night

8

Home rental in Stonington

Deer Isle / Stonington

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children

from $115 / night

$800 - $1,150 / week

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from $115 / night

(1) Excellent 

29

Vacation home in Stonington

Deer Isle / Stonington

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 $130 / night

$900 - $1,375 / week

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from $130 / night

(2) Very Good 

14

Vacation home in Stonington

Deer Isle / Stonington

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Pet friendly
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 …see more

from $130 / night

$700 - $825 / week

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from $130 / night

12

Stonington Vacation home rental

Deer Isle / Stonington

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $110 / night

$650 - $900 / week

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from $110 / night

16

Stonington Vacation home rental

Deer Isle / Stonington

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Private garden
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 wal …see more

from $118 / night

$825 - $950 / week

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from $118 / night

8

Vacation home in Stonington

Deer Isle / Stonington

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
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 (tidal), with spruce trees shading the open deck running along the waterside of the home. Large windo …see more

from $135 / night

$945 - $1,365 / week

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from $135 / night

13

Stonington Vacation home rental

Deer Isle / Stonington

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Enjoy comfort and Maine charm while vacationing in this renovated and updated, two bedroom, one bath cottage . The large, wrap-around deck enjoys distant views of Stonington Harbor (and the islands!) and views of the hillside village of Stonington. Main Street is just a …see more

from $100 / night

$500 - $795 / week

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from $100 / night

(1) Excellent 

8

Vacation home in Stonington

Deer Isle / Stonington

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Pet friendly
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, th …see more

from $75 / night

$450 - $575 / week

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from $75 / night

42

Vacation home in Stonington

Deer Isle / Stonington

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
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 fir …see more

from $190 / night

$1,330 - $2,695 / week

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from $190 / night

(1) Excellent 

11

Vacation home rental

Deer Isle / Stonington

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • 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 $100 / night

$550 - $950 / week

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from $100 / night

12

Vacation home rental

Deer Isle / Stonington

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $100 / night

$500 - $750 / week

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from $100 / night

20

Vacation home rental

DownEast and Acadia Maine / Deer Isle

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
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 …see more

from $130 / night

$900 - $1,850 / week

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from $130 / night

8

Vacation home in Stonington

Deer Isle / Stonington

4 8 7 nights min

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

from $240 / night

$1,680 - $2,520 / week

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from $240 / night

(1) Very Good 

19

Vacation home in Stonington

Deer Isle / Stonington

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $130 / night

$800 - $1,350 / week

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from $130 / night

17

Home accommodation in Deer Isle

DownEast and Acadia Maine / Deer Isle

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
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 …see more

from $220 / night

$1,100 - $1,550 / week

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from $220 / night

9

Vacation home accommodation

Deer Isle / Stonington

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
East Cottage is a lovely, efficient space sitting high above the village of Stonington. East Cottage enjoys grand views of the Deer Island Thoroughfare and beyond to the many islands speckling the harbor. Enjoy being in the village and around many galleries, restaurants …see more

from $100 / night

$500 - $600 / week

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from $100 / night

(2) Very Good 

8

Stonington Vacation home rental

Deer Isle / Stonington

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
One of the most unique properties in Stonington, Maine. Located within a 5 minute walk to downtown Stonington, this recently constructed craftsman style home is located on gently sloping ledges just 120 feet from shore. Gull's Ledge is the last home on a dead end stre …see more

from $225 / night

$1,575 - $2,520 / week

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from $225 / night

20

Vacation home in Stonington

Deer Isle / Stonington

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
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 exp …see more

from $260 / night

$1,300 - $2,000 / week

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from $260 / 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

15

Vacation home in Stonington

Deer Isle / Stonington

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Pet friendly
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 th …see more

from $195 / night

$975 - $1,375 / week

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from $195 / night

25

Vacation home in Stonington

Deer Isle / Stonington

2 6 7 nights min

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

from $110 / night

$750 - $1,100 / week

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from $110 / night

(1) Excellent 

30

Sunset Vacation home rental

Deer Isle / Sunset

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $330 / night

$2,300 - $4,400 / week

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from $330 / night

18

Home rental in Stonington

Deer Isle / Stonington

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
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 midd …see more

from $290 / night

$2,000 - $2,600 / week

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from $290 / night

13

Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $160 / night

$925 - $1,000 / week

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from $160 / night

9

Stonington Vacation home rental

Deer Isle / Stonington

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Pet friendly
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 wi …see more

from $100 / night

$550 / week

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from $100 / night

(1) Excellent 

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

$1,260 - $1,470 / week

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from $180 / night

21

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Private garden
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 …see more

from $190 / night

$1,300 - $2,100 / week

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from $190 / 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. Recently FEATURED on the Cover of Maine Magazine May Issue! Floor to ceiling windows on two sides, with front deck overhanging waters of Crockett Cove. Stunning views of Rabb …see more

from $158 / night

$1,100 - $1,675 / week

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from $158 / night

21

Stonington Vacation home rental

Deer Isle / Stonington

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly
Lasky Cottage is a captivating seasonal home perched above the rocky shoreline of the rugged Maine coast. The cottage is one of the originals designed by famous local artist and home designer Emily Muir. Enjoy complete privacy and sweeping westerly views of Crockett Cov …see more

from $190 / night

$1,300 - $2,650 / week

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from $190 / 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 - $1,365 / week

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from $120 / night

21

Home rental in Sunset

Deer Isle / Sunset

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
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 …see more

from $180 / night

$1,250 - $2,200 / week

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from $180 / night

(1) Excellent 

21

Vacation home in Stonington

Deer Isle / Stonington

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Private garden
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 …see more

from $160 / night

$1,000 - $1,600 / week

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from $160 / night

23

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
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 …see more

from $140 / night

$950 - $1,400 / week

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from $140 / night

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

4 6 7 nights min

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

from $150 / night

$1,050 - $2,730 / week

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from $150 / night

8

Stonington Vacation home rental

Deer Isle / Stonington

4 6 7 nights min

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

from $186 / night

$1,300 - $1,700 / week

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from $186 / night