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

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Stonington
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406 Vacation rentals

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 $225 / night

$1,575 - $2,730 / week

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from $225 / 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

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

(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

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

8

Vacation home in Stonington

Deer Isle / Stonington

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
This homey farmhouse is situated on a narrow, wooded peninsula just an 8 minute drive from downtown Stonington. Enjoy it's outstanding shoreline and beachfront, and both eastern and western views of the Island Sea Thoroughfare, Camden Hills and nearby islands. Soft gr …see more

from $150 / night

$1,050 - $1,995 / week

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from $150 / 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

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 

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

(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 - $1,155 / week

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from $120 / 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

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

(1)  

8

Home rental in Stonington

Deer Isle / Stonington

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Ask about pets
Built in 2002, Wolfhound Cottage sits at the end of a road surrounded by moss covered boulders and tall, wind blown trees, the classic Maine forest. A short stroll through the woods brings you to Amanda Beach, an exquisite mix of sand and boulders, perfect for swimming …see more

from $150 / night

$1,050 - $1,275 / 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. 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

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

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

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

(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

(2) Very Good 

8

Stonington Vacation home rental

Deer Isle / Stonington

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Ask about children
Natural styled cottage only 50 ft from beautiful, bold, deep water ocean. The location is completely private and quiet. The views are stunning. Perfect for the true adventurer who doesn`t mind roughing it a bit. There is no electricity and no phone. Gas appliances and n …see more

from $120 / night

$835 - $895 / 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. 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

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 - $1,365 / 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 - $1,995 / week

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from $128 / 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 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 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 li …see more

from $229 / night

$1,600 - $2,995 / week

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from $229 / night

8

Deer Isle Vacation home rental

DownEast and Acadia Maine / Deer Isle

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
Curtis is a Cottage-style, post-and-beam year-round house with an inviting wrap-around deck offering southern exposure. This is a waterfront shore property in a peaceful woodland setting. The large and open living/dining areas offer lots of windows to view an ever-chan …see more

from $200 / night

$1,400 - $2,400 / week

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from $200 / night

8

Vacation home in Deer Isle

DownEast and Acadia Maine / Deer Isle

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
A secluded getaway vacation spot close to local attractions. Located on scenic Deer Isle. Walking path to Haystack! Additional amenities include: sofabed, coffee maker, highchair, lobster pot, cd, sofa bed/futon, games - all ages, outdoor grill gas. …see more

from $135 / night

$945 - $1,395 / week

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from $135 / 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

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

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 a 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. …see more

from $154 / night

$1,075 - $1,260 / week

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from $154 / 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

(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 - $1,155 / week

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from $105 / 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

Home rental in Stonington

Deer Isle / Stonington

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
Brand new house located at the top of the hill (just up the street from the historic Stonington Opera House) in downtown Stonington, Maine. Spend your vacation relaxing on the beautiful deck watching the lobsterboats in the harbor; go to the local beach and kayak; and …see more

from $214 / night

$1,500 / week

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from $214 / 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

$2,205 - $3,360 / week

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from $315 / 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

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 - $1,095 / week

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from $120 / 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

Vacation home rental

Deer Isle / Stonington

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Ask about pets
Wonderful vacation hide-away home sitting oceanside in lush wooded setting at edge of Southeast Harbor. Beautiful shorefront and outstanding views over the bay. All on one level this Emily Muir designed cottage has a cathedral beamed ceiling in the living and dining …see more

from $143 / night

$1,000 - $1,700 / week

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from $143 / night