Vacation Rentals & Cottages in Southwest Harbor

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Luxury Beach Home Million Dollar View

Plymouth house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 24 minutes

Match: Safe Private pool

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Price per night from

$1,031

Match: Safe Private pool

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Price per night from

$687

Rustico Tides Cottages - Unit 1

North Rustico cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

“Great central location in North Rustico” My family and I stayed at Rustico Tides for 4 nights in August. The cottage was very clean, tastefully decorated (loved the photographs of local scenes) and great for our needs (family of 4). Cottage is well situated (easy access to north shore attractions/Cavendish, Charlottetown etc.) Floor plan was very convenient (loved having 2 bedrooms upstairs and master on main floor). Full laundry in unit was great as was having Keurig (its the little things!!). Amenities at cottage were appreciated, (eg kids play set and outdoor pool), and Park Pass was put to good use. Would definitely stay again.

Responds fast! avg. 15 minutes

Match: Safe Private pool

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Price per night from

$209

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

  • 15 bedrooms
  • 12 bathrooms
  • sleeps 46

Match: Safe Private pool

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Price per night from

$5,096

Magical home built around Windmill with views of ocean

Centerville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Safe Private pool

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Price per night from

$1,712

BEAUTIFUL AND PEACEFUL RESORT-LIKE SPLIT LEVEL HOUSE FOR NON-SMOKERS ONLY

Worcester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Safe Private pool

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Price per night from

$172

Woodstock Mediterranean Retreat

Woodstock house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Match: Safe Private pool

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Price per night from

$859

Elegant Meadowbrook Estate for Family Gatherings, Retreats and Special Events

Marlborough manor house

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 22

Match: Safe Private pool

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Price per night from

$4,119

Match: Safe Private pool

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Price per night from

$1,716

Mt Green 3-G01

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Safe Private pool

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Price per night from

$220

Match: Safe Private pool

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Price per night from

$216

Kilburn Manor 1821 Historical house

Malone house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Safe Private pool

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Price per night from

$743

Spacious Villa With Free Parking

Charlton villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Safe Private pool

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Price per night from

$400

Elegant Newtown Getaway - High-End Amenities, Infinity Pool, Media Room

Newtown house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Safe Private pool

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Price per night from

$718

9 Bedroom Saratoga Home, Heated Pool, HotTub By Track-Lake-Town-Golf

Saratoga Springs house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 23

Match: Safe Private pool

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Price per night from

$1,657

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Camp Little Notch

Fort Ann tented camp

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 4

1 of 2 match: Private pool, Safe

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Price per night from

$58

Stylish Motel Rooms with Lakeview R5

Northville hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private pool, Safe

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Price per night from

$189

Art Deco Motel with Lake View at Great Sacandaga Lake R6

Northville house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private pool, Safe

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Price per night from

$212

HideAway Narragansett Vacation Rental - Walk to the Ocean!

Narragansett cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Private pool, Safe

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Price per night from

$149

Chickadee Chalet

Windham apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private pool, Safe

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Price per night from

$401

Woodstock Way Vacation and Concert Rentals

Mongaup Valley house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Safe, Private pool

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Price per night from

$189

Full Basement unit with gorgeous view.

Salem house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Safe, 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: Safe, Private pool

1 of 2 filters match

Price per night from

$515

Pool house

Plymouth house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 0 minutes

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$515

Fabolous with Pool and Walk to Town

Nantucket house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$3,432

Short term close to beach and ferry to Boston

Hull house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$286

On to of Wigwam

Nantucket house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$3,547

Tranquil Villa

Monroe apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$400

Newly Built Private Home & Pool In Accord, NY

Accord house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$914

Country Woodland Home

Vankleek Hill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$243

Taghkanic House Modern Architectural Masterpiece

Taghkanic villa

  • 7 bedrooms
  • 10 bathrooms
  • sleeps 15

Responds fast! avg. 1 hour 20 minutes

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$5,713

Huge Renovated Home with Heated Pool and Jacuzzi

Queensbury house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$857

The Farmhouse at Glenwood Retreats

Glenwood farmhouse

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Safe, Private pool

1 of 2 filters match

Price per night from

$1,718

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: Safe, Private pool

1 of 2 filters match

Price per night from

$1,217

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

Garrison house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 15

1 of 2 match: Safe, 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: Safe, 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: Safe, Private pool

1 of 2 filters match

Price per night from

$1,309

catskills YURT

Livingston Manor yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private pool, Safe

1 of 2 filters match

Price per night from

$201

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rentals in Southwest Harbor

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