Vacation Rentals & Cottages in Southwest Harbor

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546 cottages

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Barnstable Village Private Pool

Barnstable house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Great place to stay” The home was clean and well maintained. The pool was a huge hit with my niece and the rest of the family. We were in a great location, close to a beach, some shops and restaurants.

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$457

Luxury Beach Home Million Dollar View

Plymouth house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 24 minutes

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$1,033

Waterfront Resort in Falmouth - 5/31/24 - 6/7/24

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$173

LOVELY SAUGERTIES RENTAL (Pool)

Saugerties house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$488

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$970

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$1,263

Pool+Hot Tub+Game Room+Kings Beds+More

Wilton house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$1,722

Pool house

Plymouth house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 0 minutes

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$517

Spacious Villa With Free Parking

Charlton villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$402

Happy Minnewaska- Welcome Home

Kerhonkson house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$517

Country Woodland Home

Vankleek Hill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated) Secure parking

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Price per night from

$243

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Romantic getaway with Spa treatments

Milford house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$201

Walk to Town, Chatham Bars Carriage House

Chatham apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$603

Provincetown MA. 2 Bedroom Condo with 2 parking sp

Provincetown apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$361

THE STABLES IN THE CARRIAGE HOUSE

Kingston villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$339

Carriage House on private English Tudor Estate

Kingston house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$339

Seacroft

Stockton Springs log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“clean,quiet and comfortable” very conviently located,to all that taht mid-coast Maine has to offer. Bed was comfortable and kitchen well equiped. The outside porch was a great place to relax after a busy day,with a nice view of the beautiful gardens. Within a short distance you will find several good local resturants and shopping. Margaret is a wonderful hostess and makes you feel right at home. Also,it is a great value for anyone not needing special handicap access.

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$144

Waterfront villa, Coastal Southern Maine

Scarborough house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$1,148

Cottages by Stanhope Beach PEI - Adults only 1 or 2 bedroom

Stanhope cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$126

OWL'S NEST LODGING

Conway apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$197

Lg. House 3 BR porches Walk to Track & Downtown

Saratoga Springs house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$689

Seaside Rosehip Cottage Downeast Maine

Jonesport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$259

Marion- Village Loft ...Perfect !

Marion apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$224

The Tranquility Suites - ideal for Extended Stay

Fredericton b&b

  • 3 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$167

Nice 3 Bedrooms Apartment Close to T and Boston

Somerville private room

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$412

3 Bedroom 2 Bath Association beach

Moultonborough house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$361

Phillie's Country Comfort Space -

New Paltz b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$161

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$459

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$142

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$419

'The Castle Cottage' overlooking Lake George!

Bolton Landing castle

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 27 minutes

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$1,601

'The King's Suite' in HIGHLANDS CASTLE!

Bolton Landing private room

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 27 minutes

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$1,257

'The Royal Bedroom' in HIGHLANDS CASTLE!

Bolton Landing private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 27 minutes

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$1,257

Short term Paying Guest

Grafton house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$58

The I.B. Munson House Inn - All Bedrooms

Wallingford b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$718

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$283

Hill Top Bed & Breakfast

Fort Plain house

  • 8 bedrooms
  • 3 bathrooms
  • sleeps 18

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$1,263

Room #1 Concord Wine Hill Top B & B

Fort Plain b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Secure parking

1 of 2 filters match

Price per night from

$217

Viewing 38 of 546
rentals in Southwest Harbor

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