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

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Stonington
92 properties
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20 properties

Deer Isle

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554 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

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

(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

(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

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

16

Stonington Vacation home rental

Deer Isle / Stonington

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
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 rental

DownEast and Acadia Maine / Deer Isle

3 6 7 nights min

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

from $330 / night

$2,310 - $3,360 / week

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from $330 / night

8

Home rental in Stonington

Deer Isle / Stonington

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Ask about children
The Boat House is a charming red boat house near the water's edge, on part of a larger family oceanfront compound. It houses a cozy and well equipped studio apartment located over this adorable two bay boathouse. An exterior stairway carries you up to an open and sunny …see more

from $98 / night

$685 - $975 / week

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from $98 / 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

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 - $1,995 / week

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from $128 / 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

2 4 Min stay varies

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

from $200 / night

$1,000 - $1,200 / week

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from $200 / 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

(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

Vacation home rental

Deer Isle / Stonington

2 4 Min stay varies

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

from $90 / night

$500 - $600 / week

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from $90 / 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

(1) Excellent 

8

Apartment rental in Stonington

Deer Isle / Stonington

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Seascape Apartment is a beautiful, up-scale apartment with excellent views of Stonington Harbor and its outlying islands. It has been meticulously renovated, utilizing quality craftsmanship and decor throughout, including custom made cabinets, granite counters, stainles …see more

from $120 / night

$840 - $1,050 / week

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from $120 / 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
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

8

Home rental in Stonington

Deer Isle / Stonington

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Ask about children
  • Ask about pets
Nestled on a flower laden mini-peninsula along the shores of Stonington Harbor, this delightful little cottage has been the subject of area artists and coveted by many. It is a beautifully unique property, small in size but providing a truly incredible setting with unpa …see more

from $105 / night

$735 - $1,260 / week

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from $105 / 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 - $1,365 / week

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from $135 / 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 - $1,155 / week

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from $135 / 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 - $1,100 / week

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from $122 / 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

(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
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

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

13

Stonington Vacation home rental

Deer Isle / Stonington

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $105 / night

$695 - $850 / week

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from $105 / night

7

Vacation home in Stonington

Deer Isle / Stonington

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
The Playhouse is an authentic 1920s rustic log cabin, nestled amongst lush forest, ferns, lilies, green grasses and wildflowers, all bordering panoramic beachfront and sparkling blue ocean waters. An expansive great room, living area and dining area accommodates your e …see more

from $158 / night

$1,100 - $1,890 / week

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from $158 / 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

8

Stonington Vacation home rental

Deer Isle / Stonington

3 6 7 nights min

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

from $128 / night

$895 - $1,260 / week

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from $128 / 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

21

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 $85 / night

$550 - $650 / week

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from $85 / 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

$1,420 - $2,310 / week

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from $203 / night

(1) Excellent 

30

Sunset Vacation home rental

Deer Isle / Sunset

5 10 Min stay varies

  • 5 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

8

Vacation home rental

Deer Isle / Stonington

3 7 7 nights min

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

from $113 / night

$790 - $1,890 / week

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from $113 / night

(1) Excellent 

8

Vacation home accommodation

Deer Isle / Stonington

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Ask about children
  • Ask about pets
Relax cove side (literally) in this cozy cottage with close up views of Stonington Harbor, distant islands, and the active harbor vista of lobster boats, schooners and kayakers just outside your windows. Light-filled, open plan with cathedral ceilings, simple yet effici …see more

from $100 / night

$697 / week

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from $100 / 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
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 lus …see more

from $345 / night

$2,415 - $3,780 / week

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from $345 / 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

(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

$2,470 - $2,625 / week

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from $353 / night

8

Vacation home in Stonington

Deer Isle / Stonington

4 8 7 nights min

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

from $270 / night

$1,890 - $3,360 / week

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from $270 / 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

$2,520 - $3,675 / week

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from $360 / night