Vacation Rentals & Cottages in Southwest Harbor

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305 cottages

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.

Match: Climbing frame Sea view

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Price per night from

$631

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

Grand Etang house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Climbing frame Sea view

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Price per night from

$315

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Pleasant Forest Shores cottages #3 : So. Chatham

South Chatham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Sea view, Climbing frame

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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: Sea view, Climbing frame

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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: Sea view, Climbing frame

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Price per night from

$75

Large Modern Cabin with Hot Tub Tucked in Woods

Bethel log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

1 of 2 match: Sea view, 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: Sea view, 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: Sea view, 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: Sea view, 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: Sea view, Climbing frame

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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

1 of 2 match: Sea view, Climbing frame

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Price per night from

$916

The Jethro Peckham House

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

1 of 2 match: Sea view, Climbing frame

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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: Sea view, 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

1 of 2 match: Sea view, Climbing frame

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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: Sea view, Climbing frame

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Price per night from

$172

4 Season vacation Home Rentals, Van Buren, Maine

Van Buren house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Sea view, 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: Sea view, Climbing frame

1 of 2 filters match

Price per night from

$264

1 of 2 match: Sea view, Climbing frame

1 of 2 filters match

Price per night from

$396

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Sea view, Climbing frame

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Price per night from

$261

The Swindon House

Roseboom house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Sea view, Climbing frame

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Price per night from

$345

1 of 2 match: Sea view, Climbing frame

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Price per night from

$315

White Mountain Getaway

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Climbing frame

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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: Sea view, Climbing frame

1 of 2 filters match

Price per night from

$235

Kendall Farm Cottages

Perry cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$197

1 of 2 match: Sea view, Climbing frame

1 of 2 filters match

Price per night from

$201

Slopeside Attitash near StoryLand, White Mountains

Glen condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Climbing frame

1 of 2 filters match

Price per night from

$229

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

Cold Spring cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Sea view, Climbing frame

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Price per night from

$411

Test Property S2-Signup

Birch Harbor boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$1,033

Mobile QA Test home [TEST]

Marlborough cave house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$12

Smith Heights Vintage Waterfront Cottages- Gooch

Eastham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$328

Marina Yacht Stays

Providence yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$184

Ocean View West Main Road Residence

Little Compton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$493

Ocean Waterfront - Walk to Pemaquid Light

New Harbor house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$369

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$631

Private Safe Beach Community

Hampton apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$574

Summer Rental - Marguerite- Biddeford Pool ME

Biddeford Pool cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$493

Maine Ocean Front 2 Bedroom Cottage

Tenants Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“A Little Bit of Heaven” Several years ago I had the good fortune to rent this cottage "sight unseen" and have been returning each year for 10 or so years which tells you how much I love it here. Dream about it in the winter too. It is immaculate, close to a small beach, stores, and not too far from Rockland and Camden. If I could, I would spend the summer here and be in heaven! Tranquil, beautiful, soothing and good for the soul are some of the ways I would describe Hupper Cottage. The owners are terrific and most accommodating. In my opinion you won't find a better place to stay in Maine for rest and relaxation! Walking and sight seeing are great, and the lobster and sunsets are fabulous! Great hub for sightseeing in mid-coast Maine as well.

Responds fast! avg. 2 hours 22 minutes

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$161

AFFORDABLE WATER VIEW Cape Cod

Pocasset cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Sea view

1 of 2 filters match

Price per night from

$172

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rentals in Southwest Harbor

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