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

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122 Vacation rentals

13

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

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Ask about children
This delightful little cape sits on 7 acres of perhaps one of the areas most valuable and most admired parcels, with nearly 280 degrees of surrounding ocean views. Overlooking the causeway, causeway beach, Deer Isle bridge, multiple islands, Eggemoggin Reach, and adjac …see more

from $120 / night

$835 - $945 / week

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from $120 / night

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

$695 - $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
  • 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 $65 / night

$450 - $525 / week

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from $65 / 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

20

Vacation home in Stonington

Deer Isle / Stonington

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • 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 $215 / night

$1500 - $1900 / week

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from $215 / night

14

Vacation home in Stonington

Deer Isle / Stonington

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 $100 / night

$700 - $800 / week

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from $100 / 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

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 

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

$841 - $1365 / week

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from $120 / 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

$1995 - $3496 / week

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from $285 / night

(1) Excellent 

30

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

(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

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

19

Vacation home in Stonington

Deer Isle / Stonington

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 $108 / night

$750 - $900 / week

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from $108 / 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

14

Stonington Vacation home rental

Deer Isle / Stonington

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Stonington Harbor Condo is a bright and airy third-floor condo with panoramic views of Stonington Harbor and some of the islands beyond. The condo is conveniently located within the hustle and bustle of town, but elevated high above Main Street to allow for optimal view …see more

from $150 / night

$1050 - $1275 / week

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from $150 / 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. Step back in time to this idyllic retreat. An expansive great room accomm …see more

from $158 / night

$1100 - $1890 / week

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from $158 / 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

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) 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

15

Vacation home in Stonington

Deer Isle / Stonington

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 $140 / night

$975 - $1376 / week

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from $140 / night

(1) Excellent 

8

Home rental in Deer Isle

DownEast and Acadia Maine / Deer Isle

4 8 7 nights min

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

from $315 / night

$2205 - $3361 / week

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from $315 / 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

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 $211 / night

$1470 - $2415 / week

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from $211 / 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

$1575 - $2520 / week

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from $225 / 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

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

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

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 - $1890 / week

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from $113 / 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 $136 / night

$950 - $1400 / week

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from $136 / 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

$695 - $850 / week

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from $100 / 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 $129 / night

$900 - $1470 / week

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from $129 / night

8

Home rental in Stonington

Deer Isle / Stonington

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Outstanding privately situated contemporary near downtown Stonington. Located on multiple acres w/ ample shorefrontage on the Stonington Thoroughfare, where seafaring vessels traverse close in front of Sea Change, offering unparrelled views of Stoningtons active ocean w …see more

from $211 / night

$1470 - $2205 / week

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from $211 / night

8

Vacation home in Stonington

Deer Isle / Stonington

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Perched high overlooking Stonington Village activities is the Crows Nest. Hear the call of the seagulls , breathe the aroma of fresh sea air and see peeks of the inner harbor. Enjoy seaside village vacationing at its best in this boat themed vacation apartment on the 2n …see more

from $72 / night

$500 - $895 / week

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from $72 / night

6

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
A very private location near the village of Deer Isle and local favorite swimming spot the Lily Pond. Additional amenities include: wood stove, coffee maker, video player, highchair, lobster pot, outdoor grill charcoal. …see more

from $93 / night

$650 / week

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from $93 / 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

(1) Excellent 

21

Vacation home in Stonington

Deer Isle / Stonington

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • 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 $143 / night

$1000 - $1600 / week

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from $143 / night