Vacation Rentals & Cottages in Southwest Harbor

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415 cottages

Island Beauty With A View

North Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$264

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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$260

The Swindon House

Roseboom house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$344

Modern Luxe Loft

Needham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

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Pleasant Forest Shores cottages #Apt : So. Chatham

South Chatham cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$75

Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$102

Pleasant Forest Shores cottages #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$115

Large Modern Cabin with Hot Tub Tucked in Woods

Bethel log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

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Price per night from

$859

Tree Tops Cottages. Up to 4 cottages available.

South Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$247

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".

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$269

Ocean View Cape on 14 Private Acres

Searsport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$373

Beautiful new house + classic cottage Seal Harbor

Seal Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$916

Camp Little Notch

Fort Ann tented camp

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 4

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$58

Stylish Motel Rooms with Lakeview R5

Northville hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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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

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Price per night from

$212

4 Season vacation Home Rentals, Van Buren, Maine

Van Buren house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$205

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Price per night from

$395

Waterfront home - Spectacular Sunsets

Bourne house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

“Peace & Tranquility” I have stayed here 4+ times, and I come home relaxed and rejuvenated. It's centrally located in the middle of the western cape, the sunsets are perfect, we usually have meals out on the expansive deck, we bring our kayaks, watch the shipping entering the canal, walk/run/bike the canal path(both sides), cook or grill fresh seafood from local stores, enjoy the wine tastings at the Belfry, jump over to the vineyard for the day, and did I mention the sunsets? The home is roomy, light and airy, plenty of parking, just perfect for us.

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Price per night from

$630

The Jethro Peckham House

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

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Price per night from

$401

“Great time!!” This wonderful home was great for our Cape vacation! The home is beautiful and the owner's pride and love for their home shows throughout the property. The owners were excellent to work with, very professional and very responsive to inquiries. The house is beautifully decorated and extremely well stocked with everything we needed to make our vacation perfect. We appreciated all the amenities - inside and out, the huge rear deck was one of our favorite places to relax and enjoy the quiet area and the beautiful landscaping, we could even hear the waves at night. The location was very convenient to restaurants, shops and beaches and is centrally located to exploring anywhere on the Cape. We are looking forward to calling this our "home away from home" again!!!

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Price per night from

$395

Handmade House on 70 secluded acres

Cobleskill house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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$166

Waterfront Resort in Falmouth - 5/31/24 - 6/7/24

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$172

White Mountain Getaway

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$258

Ocean front, 4 bedrooms, on Cabot trail, N.S.

Grand Etang house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$315

Fall dates So Vt Mtn Cabn where memories are made and guaranteed to come back.

Mount Tabor log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 20 minutes

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Price per night from

$235

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Price per night from

$315

Chickadee Chalet

Windham apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$401

HideAway Narragansett Vacation Rental - Walk to the Ocean!

Narragansett cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 32 minutes

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Price per night from

$144

Slopeside Attitash near StoryLand, White Mountains

Glen condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$229

Rustic Countryside Cottage w/ Spa/Fire Pit/Wood Pellet Stove

Cold Spring cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$411

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Price per night from

$201

OWL'S NEST LODGING

Conway apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$196

4 BR Medford Square

Medford house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$573

Campground/RV Park,Tenting,Day camping,Swimming,Full Service to Rustic sites

Fredericton cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 9

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Price per night from

$80

Unique Two-Story Log Cabin on Special Lake - no motors

Rangeley house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$252

catskills YURT

Livingston Manor yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$201

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$101

Milton Place

Milton house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$361

Viewing 38 of 415
rentals in Southwest Harbor

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