Vacation Rentals & Cottages in Southwest Harbor

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

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Climbing frame Private outdoor pool (unheated)

All filters match

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

1 of 2 match: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$115

Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$102

Large Modern Cabin with Hot Tub Tucked in Woods

Bethel log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$860

Tree Tops Cottages. Up to 4 cottages available.

South Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), 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: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$270

Ocean View Cape on 14 Private Acres

Searsport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$373

Modern Luxe Loft

Needham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$172

Beautiful new house + classic cottage Seal Harbor

Seal Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$916

4 Season vacation Home Rentals, Van Buren, Maine

Van Buren house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$206

Island Beauty With A View

North Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$264

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

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: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$631

The Jethro Peckham House

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

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: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$396

Handmade House on 70 secluded acres

Cobleskill house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$167

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$261

The Swindon House

Roseboom house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$344

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: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$235

White Mountain Getaway

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$258

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$315

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

Grand Etang house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$315

COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE...

Garrison house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 15

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,892

Woodstock Way Vacation and Concert Rentals

Mongaup Valley house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$190

Full Basement unit with gorgeous view.

Salem house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

Happy Minnewaska- Welcome Home

Kerhonkson house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$524

Pool house

Plymouth house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 0 minutes

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$516

Short term close to beach and ferry to Boston

Hull house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$287

Country Woodland Home

Vankleek Hill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$243

The Farmhouse at Glenwood Retreats

Glenwood farmhouse

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,718

Luxury Mansion Rentals in Niskayuna, NY (USA)

Niskayuna villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 13

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,123

Daydream Mountain Art Chateau '73 | Catskill

Catskill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$687

Slopeside Attitash near StoryLand, White Mountains

Glen condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$230

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

Cold Spring cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$411

1 of 2 match: Private outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$201

Captain Gosnold Village - Studio Unit 7B

Hyannis hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$222

Summer retreat on Edgartown Great Pond with Pool.

Edgartown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$715

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rentals in Southwest Harbor

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