Vacation Rentals & Cottages in Southwest Harbor

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178 cottages

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“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

$396

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Price per night from

$396

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$261

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

$412

The Swindon House

Roseboom house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$345

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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: Bicycles available, Climbing frame

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Price per night from

$103

Pleasant Forest Shores cottages #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$115

Large Modern Cabin with Hot Tub Tucked in Woods

Bethel log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$861

Tree Tops Cottages. Up to 4 cottages available.

South Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Bicycles available, Climbing frame

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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: Bicycles available, 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: Bicycles available, Climbing frame

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Price per night from

$373

Modern Luxe Loft

Needham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$173

Beautiful new house + classic cottage Seal Harbor

Seal Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$919

Renovated Cottage near center and beaches

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 15 minutes

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$804

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: Bicycles available, Climbing frame

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Price per night from

$632

The Jethro Peckham House

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

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Price per night from

$402

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

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$173

4 Season vacation Home Rentals, Van Buren, Maine

Van Buren house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$206

Island Beauty With A View

North Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$264

1 of 2 match: Bicycles available, Climbing frame

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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: Bicycles available, Climbing frame

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Price per night from

$316

White Mountain Getaway

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Climbing frame

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Price per night from

$259

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: Bicycles available, Climbing frame

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Price per night from

$236

Ocean View West Main Road Residence

Little Compton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$493

Sleep Under the Stars, PVT River, Cabin, Camper ++

Port Jervis b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 7

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$229

Moosehead Lakefront (Mount Kineo) Cottage Rental

Rockwood cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$230

This is a family and pet friendly, non smoking

Charlottetown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$260

Nice Cozy Home In A Beautiful Gated Hemlock Farms

Pocono Lake house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$144

Breath taking Ocean Harbour Front 3 Bedroom 2 Bath

Chester condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 42 minutes

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$168

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$327

Waterfront Home on Scenic Cove

Harpswell house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$184

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$127

Pleasant Street Village Home

Vinalhaven house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$282

Modern Copake Falls Getaway

Copake Falls apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$103

“Absolute best house -” Wonderful home right on point in Bar Harbor - spend evenings watching the sunset on the rocks - only wish it had more bedrooms -

1 of 2 match: Climbing frame, Bicycles available

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Price per night from

$690

Picture Perfect Home so close to Cannon Mountain_Franconia Notch!

Franconia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Bicycles available

1 of 2 filters match

Price per night from

$247

Viewing 38 of 178
rentals in Southwest Harbor

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