Vacation Rentals & Cottages in Southwest Harbor

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112 cottages

Modern Luxe Loft

Needham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Climbing frame Solarium or roof terrace

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Price per night from

$172

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Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$102

Pleasant Forest Shores cottages #Apt : So. Chatham

South Chatham cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$75

Pleasant Forest Shores cottages #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$115

3 Bedroom, 3 Bath Spacious Condo

Ogunquit condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$360

Large Modern Cabin with Hot Tub Tucked in Woods

Bethel log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$859

Tree Tops Cottages. Up to 4 cottages available.

South Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

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: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$269

Ocean View Cape on 14 Private Acres

Searsport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$373

Beautiful new house + classic cottage Seal Harbor

Seal Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$916

Holistic and off-grid homestead

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$168

Modern Vineyard Home

Oak Bluffs house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$2,290

Boston loft Third floor condo

Brookline house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 5 minutes

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$228

Marina Yacht Stays

Providence yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$184

4 Season vacation Home Rentals, Van Buren, Maine

Van Buren house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$205

Island Beauty With A View

North Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$264

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

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.

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$630

The Jethro Peckham House

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

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!!!

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$395

Handmade House on 70 secluded acres

Cobleskill house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$166

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

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$172

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$260

The Swindon House

Roseboom house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$344

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$315

White Mountain Getaway

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$258

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

Grand Etang house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

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

1 of 2 match: Solarium or roof terrace, Climbing frame

1 of 2 filters match

Price per night from

$235

Topside MainHouse

South Orleans house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$1,227

Earth Berm House at Terra Casa Retreat Center

Plattekill house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$327

Quiet Rural Setting Near Fogland Beach

Tiverton house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$228

four season vacation rental

Tannersville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$115

Charming Newport, RI - Summer Playground and Sailing Haven

Newport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$401

Luxurious Upper Saranac Lake Home, Winter or Summer, Sleeps Up To 18!

Tupper Lake house

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$1,260

Rustic, Romantic, & Spacious Log Chalet BEST PLACE for Family, & Friends

Cape Neddick chalet

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$876

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

Boston condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$516

Cozy loghouse 5 bedrooms- Hidden gem

Fredericton cottage

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$377

Country House in Upstate NY with exclusive access!

West Oneonta house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 16

1 of 2 match: Climbing frame, Solarium or roof terrace

1 of 2 filters match

Price per night from

$458

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rentals in Southwest Harbor

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