Vacation Rentals & Cottages in Southwest Harbor

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184 cottages

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Match: Skiing – property near ski resort Smoking allowed

All filters match

Price per night from

$968

Match: Skiing – property near ski resort Smoking allowed

All filters match

Price per night from

$298

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Schlafmans Hollow Solar Camping Rental Cabin #2

Lincoln cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$91

Schlafmans Hollow Solar Camping Rental Cabin #1

Lincoln cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$91

3 bedroom all year round home

Westerly house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$802

2 Bedroom Apartment at Moody Beach

Wells apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$196

Cherrybank, an Adirondack cabin on Paradox Lake

Severance house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$344

The Gold Eagle - Cottage 4

Lake George cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$184

Villa Rosa

Misquamicut house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$573

The Forge

North Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$237

Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities)

Woodstock tented camp

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$263

Villa Rosa 2

Misquamicut apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$687

Villa Rosa A

Misquamicut apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$687

The Bear Den

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$338

Townhouse in La Savina

Newbury house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$432

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$258

catskills YURT

Livingston Manor yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$201

A mountain retreat in Middle Grove NY. 20 minutes from Saratoga!

Middle Grove house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$258

Oceanfront Paradise: Experience the best of Cape Cod

Eastham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$1,031

Millionaire Mansion Countryside Stay w/ Lrg Hottub

Chester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 15

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$619

Chatham Cape Cod Vacation Rental (15639)

Chatham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$686

New Deck, and less than 1 Mi to Beach!

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$243

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$744

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$458

Sea Breeze - W007

Wells house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Smoking allowed

1 of 2 filters match

Price per night from

$360

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$1,374

OWL'S NEST LODGING

Conway apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$196

Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!

Killington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$859

Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!

Killington house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$544

Smugglers' Notch * 3 Bedroom, Sleeps 10

Jeffersonville condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$753

four season vacation rental

Tannersville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$115

Contemporary Ski Chalet Minutes to Hiking Dining Parks

South Londonderry house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$1,444

Red House w/ Access to Sebago Cove

Naples house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$379

The Stephentown Hotel!

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$109

Unique Ski Lodge on 2000 acres

Wilmington lodge

  • 14 bedrooms
  • 16 bathrooms
  • sleeps 28

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$1,712

The Happy Place on Hunter

Hunter house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$572

Hunter Haven 2bdrm condo with Sauna

Hunter condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$228

Okemo Mountain Lodge A-108 Ski In/Ski Out

Ludlow condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Smoking allowed, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$229

Viewing 38 of 184
rentals in Southwest Harbor

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