Vacation Rentals & Cottages in Southwest Harbor

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218 cottages

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Elegant Meadowbrook Estate for Family Gatherings, Retreats and Special Events

Marlborough manor house

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 22

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$4,107

Kilburn Manor 1821 Historical house

Malone house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Private outdoor pool (heated) Staffed property

All filters match

Price per night from

$742

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Camp Little Notch

Fort Ann tented camp

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$57

Art Deco Motel with Lake View at Great Sacandaga Lake R6

Northville house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$211

Stylish Motel Rooms with Lakeview R5

Northville hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$189

Luxury Waterfront Home With Heated Pool

Orleans house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,304

On to of Wigwam

Nantucket house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$3,537

Fabolous with Pool and Walk to Town

Nantucket house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$3,423

Tranquil Villa

Monroe apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$400

Huge Renovated Home with Heated Pool and Jacuzzi

Queensbury house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$856

Newly Built Private Home & Pool In Accord, NY

Accord house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$913

Heated Pool and Hot Tub 5 Minutes to Nauset Beach

Orleans house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 39 minutes

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,215

Cavendish PEI Area - 3 Bedroom 2 Bathroom Cottage

Mayfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$237

catskills YURT

Livingston Manor yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$200

Another Slice of Paradise at Hampton Beach

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$268

Luxury home on Lake Champlain, with pool, hot tub, mooring, kayaks, and more

Charlotte house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,712

Lighthouse - Q991

Ogunquit log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$250

Captain's Quarters, close to downtown Ogunquit

Ogunquit log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$406

Seaside Vacation at Hotel Paulin

Caraquet penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$158

3 Season Cabin - sleeping porch lake trails

Mount Holly log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 58 minutes

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$103

Perfect Hideaway Cabin - lake, trails, forest, meadows

Mount Holly log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 58 minutes

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$103

Greycourt at the Kaaterskill House

Stamford private room

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$75

Gap Cove at The Seaward

Rockport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$348

The Outback E Dennis/Brewster 1 bedroom 2 Guests Only 2019 availability

East Dennis cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$200

Holistic and off-grid homestead

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$167

Back Inn Time--The Loft

Saint Albans apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$360

The Magical Treehouse - Perfect for Couples!

Paul Smiths tree house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$371

Le' Chateau Douillett (Doo-yett)

Springfield house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Staffed property

1 of 2 filters match

Price per night from

$146

Crew's Quarters at Captain Alexander’s

West Harwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$164

Master Suite at Finch Guest House near Saratoga

Broadalbin b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 40 minutes

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$126

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$283

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

Mt Green 2-D01

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$219

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$299

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Staffed property, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

Viewing 38 of 218
rentals in Southwest Harbor

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