Vacation Rentals & Cottages in Southwest Harbor

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205 cottages

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Secluded Country Getaway

Highland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Cot available Private outdoor pool (unheated)

All filters match

Price per night from

$269

Daydream Mountain Art Chateau '73 | Catskill

Catskill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

Match: Cot available Private outdoor pool (unheated)

All filters match

Price per night from

$687

LOVELY SAUGERTIES RENTAL (Pool)

Saugerties house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Cot available Private outdoor pool (unheated)

All filters match

Price per night from

$487

Adirondack Mansion!

Gloversville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 19

Match: Cot available Private outdoor pool (unheated)

All filters match

Price per night from

$630

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Sweet Farmhouse with Ocean Views

Rockland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$170

#1 - A beach place by Silver Sands Park

Milford apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 52 minutes

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$229

A Place To Relax

Clifton Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$69

White Mountain Getaway!

Gorham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$263

OWL'S NEST LODGING

Conway apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$196

"SEAGULLS NEST"

East Dennis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$189

Fabulous 4 BR, Terrific View, Steps to Bay

Brewster house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$687

Charming Downtown Mystic Getaway

Mystic house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$458

NEWLY RENOVATED BEAUTIFUL HOME

Albany house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$207

Newly Renovated 2 Floor Apartment Getaway 6 ROOM 7 BED

Springfield apartment

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$516

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$614

Rustic, Romantic, & Spacious Log Chalet BEST PLACE for Family, & Friends

Cape Neddick chalet

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$878

Birches

Severance house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$229

Oar Island

Bremen cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

“perfect” We love Oar Island. It is the perfect vacation place for families with children of different ages, or just a couple. There is hiking, sunning, relaxation, but mostly what we love about Oar Island is the isolation. It is an adventure as well, since the only way to get there is by the little motorboat. It is a getaway for certain kinds of people; but if you prefer the Marriott type of stay, this is not that kind, it is much more "out-doorsy".

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$269

Poirier's Paradise

Olmstedville log cabin

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$544

Two-Story, 3-Bedroom Family Home

Windham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$229

Ultimate Vacation Home

South Yarmouth hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 3 hours 10 minutes

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$114

Taffy Lake Retreat

Nackawic log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$171

Twin Island Lake House

Pine Plains house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$411

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$1,088

Short term close to beach and ferry to Boston

Hull house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, 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: Cot available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,719

Country Woodland Home

Vankleek Hill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Cot available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$241

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

Garrison house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 15

1 of 2 match: Cot available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,890

Woodstock Way Vacation and Concert Rentals

Mongaup Valley house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Cot available, Private outdoor pool (unheated)

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: Cot available, 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: Cot available, Private outdoor pool (unheated)

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 23 minutes

1 of 2 match: Cot available, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$516

Experience Your Jorney with Us

Mexico house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$214

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$286

Spacious Rustic Cape-Fenced Yard, Large Group, 7 mins Craigville Beach, Pet

Centerville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$241

Minutes from Popham Beach - Cozy Maine Coast Cottage

Phippsburg cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$258

2 min walk to the beach - 30 Union Wharf#3

Dennis Port condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$287

The Harborfront, Beverly/Salem, Boston North Shore

Beverly apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Cot available

1 of 2 filters match

Price per night from

$516

Viewing 38 of 205
rentals in Southwest Harbor

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