Vacation Rentals & Cottages in Southwest Harbor

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168 cottages

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Match: Private outdoor pool (unheated) Smoking allowed

All filters match

Price per night from

$968

Private Berkshire County Retreat

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Smoking allowed

All filters match

Price per night from

$686

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Schlafmans Hollow Solar Camping Rental Cabin #1

Lincoln cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$91

Schlafmans Hollow Solar Camping Rental Cabin #2

Lincoln cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$91

COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE...

Garrison house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 15

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,893

Woodstock Way Vacation and Concert Rentals

Mongaup Valley house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$190

Full Basement unit with gorgeous view.

Salem house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

Happy Minnewaska- Welcome Home

Kerhonkson house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$517

Pool house

Plymouth house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 0 minutes

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$517

Short term close to beach and ferry to Boston

Hull house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$287

The Farmhouse at Glenwood Retreats

Glenwood farmhouse

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,718

Daydream Mountain Art Chateau '73 | Catskill

Catskill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$687

Country Woodland Home

Vankleek Hill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$243

2 Bedroom Apartment at Moody Beach

Wells apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$197

Cherrybank, an Adirondack cabin on Paradox Lake

Severance house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$345

The Gold Eagle - Cottage 4

Lake George cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$339

1 of 2 match: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$1,033

Chatham Cape Cod Vacation Rental (15639)

Chatham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$686

Millionaire Mansion Countryside Stay w/ Lrg Hottub

Chester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 15

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$619

The Forge

North Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$237

Villa Rosa A

Misquamicut apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$687

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

Middle Grove house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$258

New Deck, and less than 1 Mi to Beach!

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$243

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: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$263

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$458

3 bedroom all year round home

Westerly house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$802

Sea Breeze - W007

Wells house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$360

Villa Rosa

Misquamicut house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$573

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$744

Captain Gosnold Village - Studio Unit 7B

Hyannis hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$222

Summer retreat on Edgartown Great Pond with Pool.

Edgartown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$715

New England Lake House Vacation

Barrington house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$1,146

Westward, An Adirondack Getaway

Severance house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$345

Viewing 38 of 168
rentals in Southwest Harbor

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