Vacation Rentals & Cottages in Southwest Harbor

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287 cottages

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Match: Housekeeping Included Private outdoor pool (heated)

All filters match

Price per night from

$1,722

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The I.B. Munson House Inn - Bedroom 2

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Housekeeping Included

1 of 2 filters match

Price per night from

$224

The I.B. Munson House Inn - Bedroom 1

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Housekeeping Included

1 of 2 filters match

Price per night from

$224

The I.B. Munson House Inn - Bedroom 3

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Housekeeping Included

1 of 2 filters match

Price per night from

$224

The I.B. Munson House Inn - Bedroom 4

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Housekeeping Included

1 of 2 filters match

Price per night from

$224

Luxury Waterfront Home With Heated Pool

Orleans house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,312

Fabolous with Pool and Walk to Town

Nantucket house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$3,443

On to of Wigwam

Nantucket house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$3,558

Huge Renovated Home with Heated Pool and Jacuzzi

Queensbury house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$861

Tranquil Villa

Monroe apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$402

Newly Built Private Home & Pool In Accord, NY

Accord house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$916

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: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,220

The Gene Pitney Green Room

Stafford Springs apartment

  • 1 bedroom
  • 4 bathrooms
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Housekeeping Included

1 of 2 filters match

Price per night from

$173

Another Slice of Paradise at Hampton Beach

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$270

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: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,722

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$406

Lighthouse - Q991

Ogunquit log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$251

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: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$127

Crew's Quarters at Captain Alexander’s

West Harwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$165

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$299

G301A - Managed by Loon Reservation Service - NH Meals & Rooms Lic# 056365

Lincoln hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$299

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$284

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$164

7 bedroom home sleeping 14! Located on the Bayside with private pool!

Dennis house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,000

Summer vacation paradise, with private heated pool, sleeping 8

West Dennis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$500

78 Main Street 152267

Falmouth house

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 18

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$2,143

Mt Green 2-D01

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$220

Hannah's House - in Bar Harbor, close to Acadia NP, & POOL!

Bar Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$826

Maine Wilderness Lake Island Cabin

Topsfield cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Housekeeping Included

1 of 2 filters match

Price per night from

$70

U have to C it 2 believe it ! unlike any other !

Haines Falls house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 25

1 of 2 match: Private outdoor pool (heated), Housekeeping Included

1 of 2 filters match

Price per night from

$1,148

Viewing 38 of 287
rentals in Southwest Harbor

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