Vacation Rentals & Cottages in Southwest Harbor

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UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Climbing frame Housekeeping Included

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Price per night from

$261

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Pleasant Forest Shores cottages #2 : So. Chatham

South Chatham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, Climbing frame

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Price per night from

$103

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 #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$115

The I.B. Munson House Inn - Bedroom 1

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$225

The I.B. Munson House Inn - Bedroom 3

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$225

The I.B. Munson House Inn - Bedroom 2

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Housekeeping Included

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Price per night from

$225

The I.B. Munson House Inn - Bedroom 4

Wallingford b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Housekeeping Included

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Price per night from

$225

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

$863

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

$248

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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Price per night from

$271

The Gene Pitney Green Room

Stafford Springs apartment

  • 1 bedroom
  • 4 bathrooms
  • sleeps 2

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Price per night from

$173

Modern Luxe Loft

Needham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$173

Ocean View Cape on 14 Private Acres

Searsport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$374

Beautiful new house + classic cottage Seal Harbor

Seal Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$920

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

$206

Island Beauty With A View

North Hero cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$265

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Price per night from

$397

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

$633

The Jethro Peckham House

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

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Price per night from

$403

“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

$397

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

$173

The Swindon House

Roseboom house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$345

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

Grand Etang house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Housekeeping Included, Climbing frame

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Price per night from

$317

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Price per night from

$317

White Mountain Getaway

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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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

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Price per night from

$236

U have to C it 2 believe it ! unlike any other !

Haines Falls house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 25

1 of 2 match: Climbing frame, Housekeeping Included

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Price per night from

$1,150

Maine Wilderness Lake Island Cabin

Topsfield cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$71

Salisbury Coastal Retreat

Salisbury studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Housekeeping Included

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Price per night from

$196

Canada's Rotating House, Suites, & Tours (Condo #2)

North Rustico condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$117

Fabulous 2 Bedroom in Historic Cape Style House

Provincetown house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 1 hour 42 minutes

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Price per night from

$460

Slopeside Attitash near StoryLand, White Mountains

Glen condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Housekeeping Included, Climbing frame

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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: Housekeeping Included, Climbing frame

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Price per night from

$413

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Price per night from

$202

Rogers Island Get-Away Bed and Breakfast

Kensington b&b

  • 1 bedroom
  • 3 bathrooms
  • sleeps 2

1 of 2 match: Climbing frame, Housekeeping Included

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Price per night from

$131

Marion- Village Loft ...Perfect !

Marion apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Housekeeping Included

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Price per night from

$225

Viewing 38 of 229
rentals in Southwest Harbor

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