Vacation Rentals & Cottages in Southwest Harbor

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253 cottages

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Fernwood, Quiet Adirondack Getaway

Severance house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Boat available Smoking allowed

All filters match

Price per night from

$345

Westward, An Adirondack Getaway

Severance house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Boat available Smoking allowed

All filters match

Price per night from

$345

Sleep Under the Stars, PVT River, Cabin, Camper ++

Port Jervis b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 7

Match: Boat available Smoking allowed

All filters match

Price per night from

$229

Cherrybank, an Adirondack cabin on Paradox Lake

Severance house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Boat available Smoking allowed

All filters match

Price per night from

$345

Beautiful big house and chalet 4000m2 full garden

Cabaceiras do Paraguacu house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Boat available Smoking allowed

All filters match

Price per night from

$492

Pinebrook, A Peaceful Adirondack Retreat

Severance house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Boat available Smoking allowed

All filters match

Price per night from

$345

Eastward, delightful house on Paradox Lake

Severance house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Boat available Smoking allowed

All filters match

Price per night from

$353

Lakemont at the Lake

Severance house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Boat available Smoking allowed

All filters match

Price per night from

$345

Mirror Cove, Lakefront house right on Paradox Lake

Severance house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Boat available Smoking allowed

All filters match

Price per night from

$337

Birches

Severance house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Boat available Smoking allowed

All filters match

Price per night from

$230

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Old Forge house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 1

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$155

Camp Little Notch

Fort Ann tented camp

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 4

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$58

Primitive cabin on Penobscot River.

Milford house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$82

Off Grid with Cabin and Lean to

Gloversville lodge

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$115

Classic Adirondack Waterfront Cabin *Pets ok* 3/2

Saranac Lake log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 2 minutes

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$431

Authentic Adirondack Cabin-peace, quiet, nostalgia

Saranac Lake log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$402

Schlafmans Hollow Solar Camping Rental Cabin #2

Lincoln cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Boat available, 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: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$91

Cozy 1 bedroom house in Rockport Village

Rockport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$144

Charming Early 1900s Lakeside Cottage

Rangeley house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$230

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: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$104

Cabin Deck House - Formidable Cabin in Laurel Island

East Hampton log cabin

  • 4 bedrooms
  • 1 bathroom
  • sleeps 10

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$852

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: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$104

We do not list on this site

Old Forge cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 1

1 of 2 match: Smoking allowed, Boat available

1 of 2 filters match

Price per night from

$218

2 Bedroom Apartment at Moody Beach

Wells apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$197

The Gold Eagle - Cottage 4

Lake George cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$184

Villa Rosa 2

Misquamicut apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$689

The Bear Den

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$339

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$259

Townhouse in La Savina

Newbury house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$431

catskills YURT

Livingston Manor yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$201

Oceanfront Paradise: Experience the best of Cape Cod

Eastham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$1,033

Millionaire Mansion Countryside Stay w/ Lrg Hottub

Chester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 15

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$620

Villa Rosa

Misquamicut house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$574

Villa Rosa A

Misquamicut apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$689

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: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$263

New Deck, and less than 1 Mi to Beach!

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$244

The Forge

North Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Boat available, Smoking allowed

1 of 2 filters match

Price per night from

$238

Viewing 38 of 253
rentals in Southwest Harbor

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