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

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54 Vacation rentals

(7) Excellent 

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 - $1200 / week

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from $122 / night

(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 $120 / night

$795 - $910 / week

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from $120 / night

(2) Excellent 

21

Southwest Harbor Vacation condo rental

Mount Desert Island / Southwest Harbor

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Air conditioning
VACATION RENTAL - IN BEAUTIFUL SOUTHWEST HARBOR MAINE!! NR ACADIA NATIONAL PARK AND BAR HARBOR!!!!! NOW TAKING BOOKINGS FOR 2016!!! IF YOU ARE LOOKING FOR AN EARLY SPRING GET AWAY OR BOOKING YOUR SUMMER BREAK IN BEAUTIFUL ACADIA NATIONAL PARK OR LOOKING FOR AUTUMN / …see more

from $110 / night

$795 - $895 / week

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from $110 / night

(2) Excellent 

22

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Welcome to Peak A View Cottage! This open style home is 1800 sq. ft. The 1st floor has a queen bdrm, 2 dining areas, kitchen, 3/4 bath, living room, & laundry room. The 2nd floor has 3 bdrms (1 King, 1 queen, & 2 twins) and a full bath. The home is adjacent to a retail …see more

from $236 / night

$1650 - $1800 / week

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from $236 / night

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

$2000 / week

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from $286 / 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 - $1260 / week

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from $142 / 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
Rent our comfortable and spacious home, located on the Shore Road between the Hinckley and Manset Town docks. Perched atop a former warehouse, it is surrounded by a huge deck, and affords spectacular views of Southwest Harbor and the mountains of Acadia National Park. …see more

from $222 / night

$1550 - $1850 / week

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from $222 / night

(2) Excellent 

12

Vacation condo with golf nearby in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
This two bedroom, two bath condo was newly built in 2013. It is located off Main Street in Southwest Harbor, Maine and is within walking distance from town. It is only 15-20 minutes from Acadia National Park and is 5-7 minutes from the very popularly photographed Bas Ha …see more

from $185 / night

$1295 / week

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from $185 / night

(9) Very Good 

11

Vacation apartment with golf nearby in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $120 / night

$795 - $1015 / week

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from $120 / night

7

Vacation apartment in Southwest Harbor

Mount Desert Island / Southwest Harbor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $150 / night

$875 - $950 / week

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from $150 / night

8

Vacation cottage in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $215 / night

$1500 - $1900 / week

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from $215 / night

(1) Excellent 

15

Southwest Harbor Vacation home rental

Mount Desert Island / Southwest Harbor

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
The Captain's House is a beautiful, spacious, newly renovated charmer. Enjoy partial views of the harbor and easy walking to down town shops, restaurants, galleries, library, trails, and golf course it is easy to see why you will want to stay here. The first floor has a …see more

from $372 / night

$2600 - $3600 / week

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from $372 / 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 …see more

from $258 / night

$1800 - $3100 / week

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from $258 / night

5

Vacation apartment rental

Mount Desert Island / Southwest Harbor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in the village of Southwest Harbor this 2,400 square foot oceanfront townhouse offers beautiful views of Great Harbor. Three decks and heated pool makes our home a dream for families and couples alike. The interior is well appointed with hardwood floors, firep …see more

from $250 / night

$1700 - $2400 / week

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from $250 / night

8

Southwest Harbor Vacation home rental

Mount Desert Island / Southwest Harbor

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
Our Guest Cottage is designed to be shared by two couples or a family with up to three children. It is fully equipped, including use (at your risk however) of our canoe. The property is superbly located at the tip of Clark Point, which lies between Southwest Harbor …see more

from $208 / night

$1450 / week

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from $208 / night

11

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
Cedar View is a sweet cottage in an excellent location. It is tucked in the woods on 16 acres of land that abuts Acadia National Park. Very private setting but easily accessible to town, the harbor and many great hikes. It is located on picturesque Fernald Point Road. A …see more

from $172 / night

$1200 / week

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from $172 / night

16

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
If the Quietside of Mount Desert Island is what you are looking for, then Hidden Elm is a great house to enjoy all that Southwest Harbor has to offer without having to get in your car to get there. It’s a short walk to restaurants, a library, galleries and a great lobst …see more

from $258 / night

$1800 - $2500 / week

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from $258 / 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

$2700 / week

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from $386 / night

10

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Ask about children
Tiny house in Southwest Harbor! Sit around the fire pit, walk into town, down to Beal's Lobster Pound or relax in this wonderfully well appointed cottage for two (or three). This newly renovated cottage is quaint but has all that you would need. A full eat in kitchen, l …see more

from $129 / night

$900 - $1000 / week

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from $129 / night

14

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 12 Min stay varies

  • 3 bedrooms
  • Sleeps 12
  • 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 $100 / night

$1300 - $1500 / week

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from $100 / 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 $243 / night

$1700 - $2400 / week

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from $243 / night

20

Vacation home 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 $286 / night

$2000 - $2400 / week

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from $286 / night

14

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Ask about children
Located just down the road from Hinckley’s Boat Yard, one mile outside of Southwest Harbor, Sea Ledges boasts one of the most beautiful waterfront views on the island. With seven bedrooms and five baths, Sea Ledges offers old world elegance that can accommodate almost a …see more

from $1000 / night

$7000 - $9500 / week

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from $1000 / night

20

Home rental in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Pet friendly
Situated on 9 acres on the crest of Freeman Ridge, this house enjoys commanding 180 degree views over the village of Southwest Harbor, Somes Sound, Bear Island and the mountains of Acadia. A beautiful ironwood deck surrounded with professional landscaping and perennial …see more

from $200 / night

$1400 - $2400 / week

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from $200 / night

8

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
We are wonderfully located at the tip of Clark Point with out own beach, rocks, and tidepools. Four bedrooms, 2 1/2 baths, two porches, LR, DR, fully equipped kitchen, etc. to accommodate up to 8 guests. Our property is just down the beach from SW Harbor's historic Cl …see more

from $450 / night

$3150 / week

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from $450 / night

(2) Excellent 

17

Southwest Harbor Vacation home rental

Mount Desert Island / Southwest Harbor

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
Overlooking the ocean with room to stretch out on the lawn and on her decks, "The Cape Cod House" elicits relaxation right away. Plus, being so close to Southwest Harbor's shops, restaurants, galleries, all within walking distance, makes the location of this cottage all …see more

from $143 / night

$1000 - $1400 / week

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from $143 / night

10

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Pet friendly
Enjoy your own private beach or relax on the deck when you stay at this duplex property adjoining the neighboring Clarkside. Southside is near the village amenities of Southwest Harbor, and shares a lane with the Claremont Hotel, perfectly situated for strolling over fo …see more

from $158 / night

$1100 - $2200 / week

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from $158 / night

19

Vacation home rental

Mount Desert Island / Southwest Harbor

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Pet friendly
29 Sail Mountain Road is home to this wonderful hidden gem called "Diamond Rock." Very distant views of the ocean can be enjoyed, especially from the Captain's Watch. The entry leads up to a large open main room offering a living space with fireplace, two dining areas, …see more

from $429 / night

$3000 - $3600 / week

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from $429 / night

13

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
**Rates for parties up to 6 people. Each additional guest $150 per person to a maximum of 8 people.** This immaculate in-town house provides all the comfort you need with four bedrooms and two baths, and a great proximity to the village of Southwest Harbor's shops and r …see more

from $158 / night

$1100 - $2000 / week

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from $158 / night

14

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 $358 / night

$2500 / week

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from $358 / night

13

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 $172 / night

$1200 - $2400 / week

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from $172 / night

8

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
Take in the Quiet Side of Mount Desert Island from this comfortable three bedroom home in Manset. Beach access is minutes away down a short residential lane, and Seawall beach with Wonderland and Ship Harbor Trail are just around the corner. Summer Song offers a small k …see more

Pricing unknown

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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

$1200 / week

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from $180 / night

(1) Very Good 

11

Vacation home rental

Mount Desert Island / Southwest Harbor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
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 the marina, both lobster and pleasure. Eagles have been known to perch on t …see more

from $215 / night

$1500 - $2000 / week

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from $215 / night

13

Home rental in Southwest Harbor

Mount Desert Island / Southwest Harbor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Located right in Southwest Harbor, just before Seawall Road, "The Bungalow" is an opportunity to stay centrally on Mount Desert Island and close to all of Acadia National Park's wonder. Visit the Bass Harbor Lighthouse, only a few miles away, have a picnic at Seawall Be …see more

from $143 / night

$1000 - $1400 / week

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from $143 / night

14

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Pet friendly
This cozy cottage not only has a lovely wooded setting, but also a right of way to the ocean, so a short stroll from the yard takes you to one of the best private beaches on the island! Sunnymead's interior is warm and inviting with comfortable seating in front of the w …see more

from $400 / night

$2800 - $3850 / week

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from $400 / night

13

Southwest Harbor Vacation home rental

Mount Desert Island / Southwest Harbor

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Captain's Den is centrally located in Southwest Harbor and just a short walk to downtown, close to the trails of Acadia National Park, biking, kayaking and the ocean. Southwest Harbor has a little bit of everything with shops, restaurants, a community center, banks and …see more

from $172 / night

$1200 / week

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from $172 / night

11

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Pet friendly
Fireflys and salt air will illuminate your senses as you relax among the peaceful nature that awaits you. A long line of grassy fields guide your eyes to the beautiful scenery of the Atlantic. You may enjoy this gorgeous view of the ocean that peeks through the trees wh …see more

from $258 / night

$1800 - $2800 / week

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from $258 / night

19

Southwest Harbor Vacation home rental

Mount Desert Island / Southwest Harbor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Pet friendly
Situated on a tidal inlet on the quiet side of Mount Desert Island, Tidewater is sure to be a wonderful home base to explore all this beautiful island has to offer. Located near Bass Harbor, the home of the only lighthouse on MDI, and Thurston's Lobster Pound, a local f …see more

from $158 / night

$1100 - $1850 / week

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from $158 / night

10

Vacation home in Southwest Harbor

Mount Desert Island / Southwest Harbor

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
This location has it all for those looking to be near park trails and town, and still maintain a private setting when they return home for the day. Set atop Sail Mountain, Pine Knoll is spacious and bright, enjoys air conditioning, a large deck with hot tub, and a lovel …see more

Pricing unknown

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1