Vacation Rentals & Cottages in Southwest Harbor

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399 cottages

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Secluded Country Getaway

Highland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Housekeeping Included Private pool

All filters match

Price per night from

$269

Abigail ‘s Nest

Brimfield house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Housekeeping Included Private pool

All filters match

Price per night from

$1,031

Adirondack Mansion!

Gloversville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 19

Match: Housekeeping Included Private pool

All filters match

Price per night from

$630

Match: Housekeeping Included Private pool

All filters match

Price per night from

$1,718

Match: Housekeeping Included Private pool

All filters match

Price per night from

$1,260

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

Wilton house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Housekeeping Included Private pool

All filters match

Price per night from

$1,718

These homes match some but not all of your filters. Clear all filters

The I.B. Munson House Inn - Bedroom 1

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$224

The I.B. Munson House Inn - Bedroom 2

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private pool, 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 pool, 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 pool, Housekeeping Included

1 of 2 filters match

Price per night from

$224

The Gene Pitney Green Room

Stafford Springs apartment

  • 1 bedroom
  • 4 bathrooms
  • sleeps 2

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$172

Fabulous 2 Bedroom in Historic Cape Style House

Provincetown house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 1 hour 42 minutes

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$458

Maine Wilderness Lake Island Cabin

Topsfield cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private pool, 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 pool, Housekeeping Included

1 of 2 filters match

Price per night from

$1,145

Canada's Rotating House, Suites, & Tours (Condo #2)

North Rustico condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$117

Salisbury Coastal Retreat

Salisbury studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$195

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

Garrison house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 15

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$1,890

Daydream Mountain Art Chateau '73 | Catskill

Catskill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$687

Luxury Waterfront Home With Heated Pool

Orleans house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$1,309

Woodstock Way Vacation and Concert Rentals

Mongaup Valley house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$189

Full Basement unit with gorgeous view.

Salem house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Housekeeping Included, Private pool

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: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$516

Pool house

Plymouth house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 0 minutes

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$516

Taghkanic House Modern Architectural Masterpiece

Taghkanic villa

  • 7 bedrooms
  • 10 bathrooms
  • sleeps 15

Responds fast! avg. 1 hour 20 minutes

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$5,725

Huge Renovated Home with Heated Pool and Jacuzzi

Queensbury house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$859

Tranquil Villa

Monroe apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$401

Country Woodland Home

Vankleek Hill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$243

The Farmhouse at Glenwood Retreats

Glenwood farmhouse

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$1,718

Fabolous with Pool and Walk to Town

Nantucket house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$3,435

Short term close to beach and ferry to Boston

Hull house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$287

Newly Built Private Home & Pool In Accord, NY

Accord house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$916

On to of Wigwam

Nantucket house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Housekeeping Included, Private pool

1 of 2 filters match

Price per night from

$3,550

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 pool

1 of 2 filters match

Price per night from

$1,220

Rogers Island Get-Away Bed and Breakfast

Kensington b&b

  • 1 bedroom
  • 3 bathrooms
  • sleeps 2

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$130

Marion- Village Loft ...Perfect !

Marion apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$224

Seaside Vacation at Hotel Paulin

Caraquet penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$159

Memories of Meadowbank.

Clyde River cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$205

The I.B. Munson House Inn - All Bedrooms

Wallingford b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private pool, Housekeeping Included

1 of 2 filters match

Price per night from

$716

Viewing 38 of 399
rentals in Southwest Harbor

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