50 Best Vacation Rentals in Stonington - Holiday Lettings - Cabins

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326 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) 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

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

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

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

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

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

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 

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

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

12

Vacation home in Stonington

Deer Isle / Stonington

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
Tide Watcher 1 is a handicapped-accessible apartment in Stonington’s picturesque village. Watch the boats and the tides come and go from this nicely equipped seaside efficiency apartment. The apartment has tile floors, many new and contemporary furnishings as well as a …see more

from $80 / night

$500 - $700 / week

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from $80 / night

(1) Excellent 

19

Vacation home in Stonington

Deer Isle / Stonington

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
Pleasant View is a bright and cheery New Englander style house located on a quiet cul-de-sac in the heart of Stonington village. Enjoy views of Stonington harbor, a clean and fresh space with all the conveniences of home and an artist/writing retreat with views of the t …see more

from $110 / night

$750 - $900 / week

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from $110 / 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

17

Stonington Vacation home rental

Deer Isle / Stonington

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Tarnavik is a cherished family home at the end of a private drive on Indian Point Road in Stonington. Enjoy a spacious, oceanfront cottage with all the conveniences of home including wireless internet, satellite television and telephone. Tarnavik was built in the early …see more

from $230 / night

$1,600 - $2,600 / week

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from $230 / night

9

Vacation home in Stonington

Deer Isle / Stonington

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
West Cottage is a bright and clean efficiency cottage sitting high above the village of Stonington. West 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, …see more

from $90 / night

$500 - $650 / week

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from $90 / night

16

Vacation home in Stonington

Deer Isle / Stonington

2 4 Min stay varies

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

from $122 / night

$850 - $950 / week

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from $122 / 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 Stonington

Deer Isle / Stonington

4 14 7 nights min

  • 4 bedrooms
  • Sleeps 14
  • 7 nights min
  • Ask about children
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: …see more

from $285 / night

$1,995 - $3,495 / week

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from $285 / 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

20

Vacation home in Stonington

Deer Isle / Stonington

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Private garden
Tide Watcher 2 is a well-decorated apartment on West Main Street in Stonington’s seaside village. Enjoy watching the boats and tides come and go from this bright and airy in-town location. Tide Watcher 2 is a two bedroom, one bathroom apartment. The space has an attract …see more

from $115 / night

$800 - $1,200 / week

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from $115 / 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

8

Stonington Vacation home rental

Deer Isle / Stonington

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Ask about pets
Privately situated on a portion of a larger oceanfront compound, 'The Carriage House' is a charming apartment located above a four bay boat house. Glimpses of the nearby oceanfront peak through the lush forested setting. Exterior stairs carry you up to this second story …see more

from $105 / night

$735 - $945 / week

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from $105 / night