Vacation Rentals & Cottages in Southwest Harbor

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4 Season vacation Home Rentals, Van Buren, Maine

Van Buren house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Climbing frame Smoking allowed

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Price per night from

$206

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Pleasant Forest Shores cottages #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$115

Pleasant Forest Shores cottages #Apt : So. Chatham

South Chatham cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$75

Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$102

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

$860

Tree Tops Cottages. Up to 4 cottages available.

South Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$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".

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$270

Ocean View Cape on 14 Private Acres

Searsport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$373

Modern Luxe Loft

Needham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Beautiful new house + classic cottage Seal Harbor

Seal Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$918

Island Beauty With A View

North Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$264

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Price per night from

$396

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.

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$631

The Jethro Peckham House

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

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Price per night from

$402

“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!!!

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$396

Handmade House on 70 secluded acres

Cobleskill house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$167

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

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$261

The Swindon House

Roseboom house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$344

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Price per night from

$316

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

Grand Etang house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$316

White Mountain Getaway

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$258

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

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$235

Schlafmans Hollow Solar Camping Rental Cabin #2

Lincoln cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Smoking allowed

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Price per night from

$91

Schlafmans Hollow Solar Camping Rental Cabin #1

Lincoln cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$91

Slopeside Attitash near StoryLand, White Mountains

Glen condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$230

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Price per night from

$201

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

Cold Spring cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Smoking allowed, Climbing frame

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Price per night from

$411

2 Bedroom Apartment at Moody Beach

Wells apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$196

Cherrybank, an Adirondack cabin on Paradox Lake

Severance house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Smoking allowed

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Price per night from

$344

The Gold Eagle - Cottage 4

Lake George cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Smoking allowed

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Price per night from

$184

Villa Rosa 2

Misquamicut apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Smoking allowed

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Price per night from

$688

The Bear Den

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Smoking allowed

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Price per night from

$339

Townhouse in La Savina

Newbury house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Climbing frame, Smoking allowed

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Price per night from

$433

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Price per night from

$258

catskills YURT

Livingston Manor yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Smoking allowed

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Price per night from

$201

Oceanfront Paradise: Experience the best of Cape Cod

Eastham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Climbing frame, Smoking allowed

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Price per night from

$1,032

Millionaire Mansion Countryside Stay w/ Lrg Hottub

Chester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 15

1 of 2 match: Climbing frame, Smoking allowed

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Price per night from

$620

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rentals in Southwest Harbor

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