50 Best Vacation Rentals in Southwest Harbor - Holiday Lettings - Cabins

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560 Vacation rentals

(3) Very Good 

Certificate of Excellence

17

Apartment rental in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Located in Southwest Harbor known as the quiet side of Mount Desert Island which is the home to Acadia National Park and Bar Harbor. Minutes from downtown shops and restaurants.The property is set back off Main Street and next to the golf course! The property is less …see more

Certificate of Excellence

from $135 / night

$950 - $1,150 / week

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from $135 / night

(4) Very Good 

21

Southwest Harbor Vacation condo rental

Mount Desert Island / Southwest Harbor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
VACATION RENTAL - IN BEAUTIFUL SOUTHWEST HARBOR MAINE!! NR ACADIA NATIONAL PARK AND BAR HARBOR! IF YOU ARE LOOKING FOR AN EARLY SPRING GET AWAY OR BOOKING YOUR SUMMER BREAK IN BEAUTIFUL ACADIA NATIONAL PARK OR LOOKING FOR AUTUMN / FALL WHICH MAKES A GREAT TIME TO SEE …see more

from $135 / night

$950 - $1,150 / week

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from $135 / night

4

Vacation cottage in Southwest Harbor

Mount Desert Island / Southwest Harbor

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
Newly built/designed & well appointed cabin nestled in the woods for a real Maine experience. This one bedroom with loft cabin is warm and cozy. Gas fireplace & has all the amenities one would need to begin and end a perfect day in Acadia National park. Situated very cl …see more

from $250 / night

$1,750 / week

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from $250 / night

(1) Excellent 

22

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Located in Manset, 2 miles south of Southwest Harbor, this classic New England farmhouse has 4 bedrooms, 2.5 baths, living room, kitchen, dining room, laundry, back deck and front porch with spectacular views of mountains and harbor. Fully furnished and equipped for you …see more

from $386 / night

$2,700 / week

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from $386 / night

(10) Very Good 

15

Southwest Harbor Vacation home rental

Mount Desert Island / Southwest Harbor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Car not necessary
Harbors End cottage is located in Southwest Harbor on the 'Quiet Side' of Mt. Desert Island directly across the street from the harbor. This charming, sunny and very cozy space is 900 sq. feet, 2 story, 2 bedroom, 2 bathroom. Although small square footage, the downstair …see more

from $122 / night

$850 - $1,250 / week

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Responds fast!
avg. 1 hour 15 minutes

from $122 / night

27

Southwest Harbor Vacation studio rental

Mount Desert Island / Southwest Harbor

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
For a true Maine experience, stay in this comfortable studio suite directly across the street from the harbor. You'll have inviting amenities, beautiful harbor views, and a great location near the harbor and local dockside restaurants. Situated on the water in Southwe …see more

from $100 / night

$700 / week

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Responds fast!
avg. 52 minutes

from $100 / night

20

Home rental in Southwest Harbor with golf nearby

Mount Desert Island / Southwest Harbor

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Private garden
This two bedroom cape and studio cabin with sleeping loft is within walking distance of Norwood Cove, the causeway, golf, Acadia hiking trails: Flying Mt., St. Sauveur, and Acadia Mt. Only one mile to town center and one and a half miles to swimming at Echo Lake. The …see more

from $150 / night

$1,000 - $1,700 / week

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from $150 / night

(4) Very Good 

17

Southwest Harbor Vacation cottage rental

Mount Desert Island / Southwest Harbor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Quiet 3BR 2BA in a wooded setting with a beautiful harbor view. A quiet wooded setting, beautiful harbor view, and a deeded right-of-way to the rocky shore all help make this a great vacation spot. In the neighborhood of the premier boat-builders on the island and jus …see more

from $140 / night

$975 - $2,250 / week

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from $140 / night

(10) Very Good 

11

Vacation apartment with golf nearby in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Located in Southwest Harbor known as the quiet side of Mount Desert Island which is the home to Acadia National Park and Bar Harbor. Minutes from downtown shops and restaurants.The property is set back off Main Street and next to the golf course! The property is less …see more

from $135 / night

$1,050 - $1,150 / week

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from $135 / night

26

Southwest Harbor Vacation home rental

Mount Desert Island / Southwest Harbor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Alacrity means Cheerful Readiness. It is well furnished and ready to move in. The large kitchen is stocked with most popular appliances. The lower level has an entertainment center with surround sound and a projection TV and 10 foot by 8 foot screen. Each bedroom has …see more

from $343 / night

$2,400 - $4,500 / week

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from $343 / night

(1) Excellent 

7

Vacation apartment in Southwest Harbor

Mount Desert Island / Southwest Harbor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden
Bird's Nest is an elevated efficiency apartment with sweeping views of Somes Sound, the ocean, the mountains of Acadia National Park, and the lighthouse on Bear Island. At the end of a long winding private driveway Bird's Nest provides a quiet get away for a couple. The …see more

from $165 / night

$950 / week

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from $165 / night

16

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Modern 2 BR 1 BA guest house in rural Southwest Harbor on Mt. Desert Island This vacation home rental near Acadia National Park is a New England style home (1120 sq/ft) located in quiet, peaceful, wooded, residential setting in Southwest Harbor on the 'quiet side' of M …see more

from $175 / night

$825 - $1,500 / week

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from $175 / night

14

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 14 Min stay varies

  • 3 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Take a 5 minute drive to remote Cable Crossing Beach and gather fresh mussels at low tide, or drive five minutes south to Seawall Point for shell-finding and a great ocean breeze. Another five minute drive southward will take you to Acadia's Wonderland forest and the hi …see more

from $298 / night

$2,200 - $2,450 / week

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Responds fast!
avg. 2 hours 59 minutes

from $298 / night

30

Southwest Harbor Vacation studio rental

Mount Desert Island / Southwest Harbor

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Tucked away from the chaos of everyday life, this Southwest Harbor vacation rental is sure to charm guests with its laid-back interior. It's perfect for a quiet getaway for two! This studio offers a lively experience in Southwest Harbor. It's right across the street fr …see more

from $100 / night

$700 / week

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Responds fast!
avg. 1 hour 11 minutes

from $100 / night

(1) Excellent 

20

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Located 1 mile south of Southwest Harbor, this cedar-shingled saltbox overlooks the harbor and mountains of Mt. Desert Island and is within easy access of Acadia National Park for all outdoor activities. Within walking distance of the island wide free shuttle bus. Handi …see more

from $286 / night

$2,000 / week

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from $286 / night

12

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 8 mi
  • Child friendly
The Bad News: In August, 2017, guests accidentally set the house on fire.* The Good News: The house has been completely renovated for the 2018 season! New floors, new walls, new ceilings, new kitchen cabinets and appliances, new furniture—all new! [Please note: t …see more

from $250 / night

$1,750 - $1,950 / week

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from $250 / night

(2) Excellent 

17

Vacation cottage in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
A rustic, comfortable 2 BR 2 BA cottage on a hillside in the woods, close to Acadia NP A sweet, nicely appointed cottage in a private, wooded setting is a great place to get away--adjoins the Park and close to the village of SW Harbor. It's only a short walk to the oce …see more

from $172 / night

$1,200 - $1,600 / week

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from $172 / night

(3) Excellent 

32

Vacation apartment in Southwest Harbor

Mount Desert Island / Southwest Harbor

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 3 mi
  • Child friendly
Seaview Quarters is an idyllic 2nd floor suite designed in 2015 that was inspired by the natural beauty of the Maine Coast and is part of an architecturally designed three story home. It offers a great room enclosed by three walls of windows that includes a kitchen, di …see more

from $142 / night

$990 - $1,260 / week

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Responds fast!
avg. 1 hour 48 minutes

from $142 / night

13

Southwest Harbor Vacation home rental

Mount Desert Island / Southwest Harbor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Pet friendly
Hillside Cottage is less than a mile from town, Acadia National Park, a local breakfast spot, great coffee shop and so much more. This affordable, well appointed and relaxing retreat is a cottage to return to. The back yard is equipped with Adirondack chairs and a fire …see more

from $950 / night

$950 - $1,100 / week

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from $950 / night

12

Vacation home rental

Mount Desert Island / Southwest Harbor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Charming little 2 BR 1 BA cottage with privacy & spectacular harbor views Secluded waterfront cottage on Mount Desert Island in Southwest Harbor. Sitting on a bluff overlooking the inner harbor, with views of the mountains beyond. View the vessel coming and going from …see more

from $200 / night

$1,400 - $2,000 / week

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from $200 / night

8

Vacation apartment in Southwest Harbor

Mount Desert Island / Southwest Harbor

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Child friendly
Elegant one bedroom apartment located within two blocks of the center of the village of Southwest Harbor, Maine. Views of the harbor from all rooms, opens to a private deck overlooking the garden. Amenities include two gas fireplaces, Jacuzzi tub in bathroom, cable, WiF …see more

from $225 / night

$1,400 / week

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from $225 / night

26

Southwest Harbor Vacation studio rental

Mount Desert Island / Southwest Harbor

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Enjoy picturesque harbor views from every window at this studio-style Southwest Harbor retreat, a beautifully situated waterfront suite with an ideal location for lighthouse lovers, kayakers, and visitors to Acadia National Park. Scenically positioned in the charming …see more

from $100 / night

$700 / week

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Responds fast!
avg. 1 hour 12 minutes

from $100 / night

8

Vacation cottage in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Sea Watch, a three-bedroom cottage located on Sawyer's Cove with a path to the shore in Seal Cove. The cottage is cozy, secluded and in a peaceful located near beautiful Pretty Marsh Harbor. Spectacular Sunsets! Free-standing wood stove makes your nights extra cozy. …see more

from $272 / night

$1,900 / week

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Responds fast!
avg. 3 hours 55 minutes

from $272 / night

5

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Oceanfront, 4 bedroom home with dock, near Acadia National Park. On private road, but walking distance to town of Southwest Harbor. Fully furnished. …see more

from $500 / night

$3,500 - $4,340 / week

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Responds fast!
avg. 2 hours 56 minutes

from $500 / night

11

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
A modern, well-appointed and comfortable 3 BR 2 BA home on Mt Desert Island Want all the comforts of home in a newer, well-built cottage in a private setting but close to a village with its shops and restaurants? Want to be close to Acadia National Park and less than 3 …see more

from $300 / night

$2,100 - $2,450 / week

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from $300 / night

(1) Excellent 

19

Vacation cottage in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Private, nicely-appointed, well-maintained in the woods near Southwest Harbor This 3000 sq ft house is in an excellent location - tucked in the woods on 12 acres of land that abuts Acadia National Park and the historic Carroll Farm Homestead. Very private setting ( dee …see more

from $300 / night

$2,100 / week

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from $300 / night

28

Home rental in Southwest Harbor

Mount Desert Island / Southwest Harbor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Come home to cherish Maine with a holiday on Ravenspoint. 1500 feet of ocean front, 9.75 acres, a five acre field, meadows, rocky shoreline to the north and private pebble beach to the south, those distant tranquil mountains that your guests always drool over, sunsets f …see more

from $22,000 / night

$22,000 / week

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from $22,000 / night

(1) Excellent 

39

Home rental in Southwest Harbor

Mount Desert Island / Southwest Harbor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
Make a memorable summer escape to this four-bedroom Southwest Harbor home, a well-equipped family property with a private deck, a lovely yard with a firepit and a picnic area, and an ideal location for visiting Acadia National Park. This sun-splashed home is located i …see more

from $114 / night

$798 / week

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Responds fast!
avg. 56 minutes

from $114 / night

14

Vacation cottage in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
Updated 2 BR cottage in a neighborhood near the village of Southwest Harbor A beautifully updated little 2 BR cottage near the village of Southwest Harbor; in a quiet residential neighborhood, set back from the street, it's a great place to serve as your home base for …see more

from $136 / night

$950 - $1,100 / week

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from $136 / night

12

Vacation home with shared pool in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Ask about children
You'll have many opportunities to watch for Mermaids from this spacious townhome: from the deck of the main living space and the master bedroom you'll have views of Southwest Harbor and the ocean, or perhaps a glimpse of one taking a dip in the heated swimming pool belo …see more

from $1,750 / night

$1,750 - $2,400 / week

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from $1,750 / night

(1) Excellent 

25

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
Welcome to Customs House an oasis of peace and serenity that combines 19th century charm with 21st century convenience. Built in 1858, extensively remodeled in 2003, and newly furnished in 2013, Customs House offers comfortable spaces throughout to relax, gracious new M …see more

from $1,800 / night

$1,800 - $3,100 / week

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from $1,800 / night

20

Home rental in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Nepenthe Den is a newly renovated and spacious Farmhouse with partial water and mountain views conveniently located in the Heart of Southwest Harbor. Nepenthe has a fully stocked kitchen with all new stainless steel appliances including a refrigerator, 5 top burner gas …see more

from $350 / night

$2,450 / week

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from $350 / night

(5) Excellent 

10

Vacation cottage in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
A sweet retreat, this little 2 BR 2 BA cottage is well cared for and comfortable. This comfortable 2 BR cottage is perfect for those who wish to be out of the congestion of town, but within easy access of everything. At one end of the road are Somes Sound, St. Sauveur, …see more

from $140 / night

$975 - $1,100 / week

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from $140 / night

(3) Excellent 

24

Vacation home rental

Mount Desert Island / Southwest Harbor

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Pet friendly
This cute camp nestled in the woods on a ridge in Southwest Harbor not only welcomes your four-legged friends, but offers a discount for people that bring their pets along! Calm Breezes is a comfortable camp with basic kitchen appliances, two bedrooms plus a sleeping lo …see more

from $850 / night

$850 - $1,225 / week

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from $850 / night

17

Southwest Harbor Vacation cottage rental

Mount Desert Island / Southwest Harbor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
Beautiful 4 BR 3 BA with harbor views, walk to the village of Southwest Harbor Handicapped accessible home on Clark Point Road in the village with a large deck across the front, overlooking scenic Southwest Harbor to the West with magnificent sunsets. It lies adjacent …see more

from $225 / night

$1,575 - $2,100 / week

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from $225 / night

13

Vacation home with shared pool in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
Four Seasons is a newly refurbished , spacious , 4 story condominium in Southwest Harbor. It is a very desirable corner unit that offers open views of the harbor and the Cranberry Islands beyond. There are decks on 3 levels giving you the opportunity to watch the activi …see more

from $1,800 / night

$1,800 - $2,500 / week

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from $1,800 / night

15

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Pet friendly
Hunt for sea glass on your own private beach from this duplex property adjoining the neighboring Southside. Clarkside and Southside are near the village amenities of Southwest Harbor, and share a lane with the Claremont Hotel, perfectly situated for strolling over for d …see more

from $1,200 / night

$1,200 - $2,400 / week

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from $1,200 / night

14

Vacation cottage in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Beautiful newer 2 BR 1.5 BA cottage near Southwest Harbor You will find this beautiful little cottage charming, comfortable and private, located on a rural, wooded plot near Southwest Harbor. The owner has personalized the open-concept cottage with well-crafted touches …see more

from $158 / night

$1,100 - $1,300 / week

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from $158 / night

13

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
This two bedroom summer cottage is nestled in the woods of Manset on the shore road, with a small pond off the deck and a peek-a-boo view of the ocean and mountains and direct access to road that runs along the ocean and through the boatyards. There are two bedrooms, a …see more

from $180 / night

$1,200 / week

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from $180 / night

(2) Excellent 

13

Vacation apartment in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Unbelieveable view from the large deck overlooking a working harbor. Lobster boats coming and going. Sailboats enjoying the harbor. Seals are visible at times. The mountains are in the distance. A heated pool for fun in the sun. We are located on Mount Desert Islan …see more

from $295 / night

$2,065 / week

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Responds fast!
avg. 2 hours 47 minutes

from $295 / night