Vacation Rentals & Cottages in Southwest Harbor

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345 cottages

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Mirror Lake Manor Olympic House

Lake Placid house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 22

Match: Games room Car not required

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Price per night from

$978

5/24-31, 2024 at Long Wharf Resort, Newport, RI

Newport hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$460

Brand New Townhouse Sleeps 8

Provincetown house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,379

This is a family and pet friendly, non smoking

Charlottetown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$261

Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

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Price per night from

$6,898

Luxurious Captains Mansion - Waterfront, Town, & Beaches - 5 stars

Edgartown house

  • 12 bedrooms
  • 7 bathrooms
  • sleeps 26

“great trip!” Definately would do it again! Loved the house and the area. Marthas Vineyard is a very special place!

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Price per night from

$903

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Price per night from

$972

East Wing of Captain's Mansion - Luxury, Waterfront, Town, & Beaches - 5 stars

Oak Bluffs house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$650

Luxurious 2BR - 2Bath W/ Gym | Downtown at Yale

New Haven apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$1,185

Sunset Mountain Estate

Monticello house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 20

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Price per night from

$682

West Wing of Captain Morse House Waterfront, Town & Beach - Pets OK, - 5 stars

Oak Bluffs house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$553

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Judge Brown House

Norwich house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

1 of 2 match: Car not required, Games room

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Price per night from

$690

4 bedroom Victorian Condo

Boston condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$574

Comfortable & well-appointed On the Line Mas & RI (1st floor)

Pawtucket apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$150

Private room in house. Albany Medical/colleges and Downtown Albany.

Albany house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Games room, Car not required

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Price per night from

$64

Private room in house. Albany Medical/colleges and Downtown Albany.

Albany house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Games room, Car not required

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Price per night from

$64

Penthouse - 1 king BR - steps to Back Bay Station!

Boston condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$518

Private room in house. Albany Medical/colleges and Downtown Albany.

Albany house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Games room, Car not required

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Price per night from

$64

Angels Landing waterfront property in center of town, Unit #18

Provincetown studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$189

Newport Adorable Apt. Historic Hill 1 Bdrm

Newport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Games room, Car not required

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Price per night from

$164

Vacation Rental

Vernon caravan/mobile home

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 36 minutes

1 of 2 match: Car not required, Games room

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Price per night from

$92

Wild Pines Cabins

Belfast cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Games room

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Price per night from

$101

Luxe One Bedroom Suite w/ Free WiFi, Resort Pool & Steps From Harbor

Newport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Games room

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Price per night from

$132

Two Bedroom Suite w/ Free WiFi, Resort Pool & Steps From Harbor

Newport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 45 minutes

1 of 2 match: Car not required, Games room

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Price per night from

$152

Ogunquit Condo - 5 Minute Walk to Footbridge Beach!

Ogunquit condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Games room, Car not required

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Price per night from

$202

Awesome Water View Penthouse

Provincetown penthouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Games room, Car not required

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Price per night from

$748

1 of 2 match: Games room, Car not required

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Price per night from

$887

Responds fast! avg. 53 minutes

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Price per night from

$107

1 minute walk to subway, 10 minutes to airport

Revere b&b

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 49 minutes

1 of 2 match: Games room, Car not required

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Price per night from

$340

Provincetown MA. 2 Bedroom Condo with 2 parking sp

Provincetown apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Games room, Car not required

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Price per night from

$361

A Park View Apartment in Hudson

Hudson apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Games room, Car not required

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Price per night from

$230

Mardals Hideaway - 3 bedroom

Golden house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Games room, Car not required

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Price per night from

$189

THE STABLES IN THE CARRIAGE HOUSE

Kingston villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Games room, Car not required

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Price per night from

$340

“Home away from home” My sisters and I rented this cottage on Labor day weekend for our annual sisters get away. Ella was very helpful giving exact directions to the cabin which is important when you are not familiar with a location. She was able to suggest many activities in the area as well as cute little restaurants/taverns in towns nearby. The cabin was truly like a home away from home. Ella clearly takes pride in the upkeep of the property. You are within walking distance to a grocery store, café, liquor store and a little store where you can find many necessities. This is a great get away for any time of the year. I am hoping to return sometime in the next year!

Responds fast! avg. 53 minutes

1 of 2 match: Games room, Car not required

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Price per night from

$113

“An Oasis By The Sea” August 30, 2012 Dear Rose & Guy- Thank you very, very much for our wonderful stay at Periwinkle Cottage! From the beautifully decorated rooms, the most comfortable beds, soft luxurious towels and linens, convenient kitchen, TV to the lovely outdoor sitting area and garden... Omg...what a gem! It is a true delight! And the cottage is immaculate and very peaceful and tranquil. We will definitely recommend your "oasis by the sea" to our family and friends! Love, Penny and Urs Westport, Connecticut

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Games room, Car not required

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Price per night from

$167

“Best weekend ever :)” I have recently rented the bungalow and just have great things to say about it. The place is so cozy, and cute, they had everything we needed and the location couldn't be better. It's very close to any of the skii resorts and many attractions, market...It was only my boyfriend and I and the bungalow was just the perfect choice to spend a holiday weekend. Ella, the owner, was very helpful providing us any info we could need. We are already planning to go back the beggining of the year and summer for sure. Thank you so much Ella!!!

Responds fast! avg. 53 minutes

1 of 2 match: Games room, Car not required

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Price per night from

$103

Fabulous Post & Beam Berkshire Rental

Monterey house

  • 2 bathrooms
  • sleeps 7

1 of 2 match: Games room, Car not required

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Price per night from

$206

Edgartown - Clean, quiet, and comfortable home close to bike trail

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Games room, Car not required

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Price per night from

$748

Viewing 38 of 345
rentals in Southwest Harbor

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