Vacation Rentals & Cottages in Southwest Harbor

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230 cottages

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

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Private outdoor pool (unheated) Wheelchair accessible

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Price per night from

$173

Match: Private outdoor pool (unheated) Wheelchair accessible

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Price per night from

$1,260

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Topside MainHouse

South Orleans house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$1,229

White Mountains, NH Resort Condo with pool

Lincoln apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

“Beautiful and highly recommended” The townhouse was clean and well maitained. There was plenty of room for four or more people. The upstairs balcony over looking the living rooom and the slider to the deck was great. There were views from just about every window. The fireplace made for a great way to relax and enjoy the townhouse. I would highly recommend this property to a friend and I plan to go back. It is close by to many attractions and restaurants. There a is a shuttle bus to Loon Mountain for skiing. I am looking forward to staying agisn next year.

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$127

Fully furnished Flat for rent,Sarba,Kaslik,Jounieh

Jounieh apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$115

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$724

Beautiful Lake Side Getaway, Quiet, and Peaceful

Winchester apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Relaxing vacation” We vacationed here for the first two weeks of July. Bill and Sandy were fabulous hosts. They were attentive to our needs and generous with their time taking us out in their boat to view the fireworks. The space is decorated tastefully and was clean and welcoming. We spent almost all of our time outdoors enjoying the sun and water. We ate most of our meals outside on the patio. The only thing that could have made it any better would have been to have a screened in area so that we could have stayed out later at night after the mosquitos' came out. We are planning on returning next year.

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$144

Cottages by Stanhope Beach PEI - Adults only 1 or 2 bedroom

Stanhope cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$126

Earth Berm House at Terra Casa Retreat Center

Plattekill house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$327

Yellow Tuna Hostel - Yellow Tuna

Wedgeport guest house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$364

Beautiful Country Home

Monticello house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$436

The Swindon House

Roseboom house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$345

Stay At Jimmy's

Woodstock b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$229

Spacious Waterfront Retreat- The Zen Den

Athol house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$224

Millionaire Mansion Countryside Stay w/ Lrg Hottub

Chester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 15

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$619

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

North Rustico condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$117

Canada's Rotating House, Suites, & Tours (Condo #3)

North Rustico condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$117

Canada's Rotating House!

North Rustico apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$117

Spring, Summer, Fall Weekend Getaway

Hudson apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$234

Abners Pondside Retreat "A" Near Cooperstown NY

Oneonta apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$345

Narragansett Rhode Island Beach Rental

Narragansett house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$394

Nice clean house 1/4 mile walk to Sesuit Harbor!

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$517

Cozy Cottage

Belle River cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$126

Ocean View Condo across from Beach with pool!

Dennis Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 34 minutes

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$172

Queen One Bedroom Suite

Winthrop hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$298

9 Perio Point

Beals house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$238

Canada's Rotating House, Suites, & Tours

North Rustico apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$117

Greenwich Moonlight Bay-Tranquility w/ Beautiful Waterview near Greenwich Beach

Saint Peters Bay cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Wonderful Cottage” My wife and I stayed at Tony & Jennifer's cottage for a week on our honeymoon this past summer. It was a wonderful experience and they were a great couple to work with! Jennifer met us at the door and showed us around the place. They have carefully provided virtually everything a guest will need during their stay there--including things we hadn't considered! The quiet, beautiful layout was perfect for our first week of married life together as we took various trips out to explore the island. Jennifer had all the tourist info there that we needed to plan our explorations of the island. My wife and I would love to come back to PEI someday and we'd definitely book Tony & Jennifer's cottage again if it were available!

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$218

house on miles pond

Concord house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 22 minutes

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$144

Great Sacandaga Lake House Rental

Northville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$173

Beautiful big house and chalet 4000m2 full garden

Cabaceiras do Paraguacu house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$491

The Church Town House

Richfield Springs hotel apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$655

The Sylvan Town House

Richfield Springs hotel apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 25

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$1,131

The Central Town House

Richfield Springs hotel apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$738

The Cape Cod Cottage with Beach Pass

Eastham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$295

July 7-13 at Inn on Long Wharf Resort,Newport, RI

Newport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$287

2 room office +wc with 1 bedroom , kitchen +bathr.

Athens apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$74

Cape Cod Cottage, 4 bedrooms, 2 baths, Eastham, MA

Eastham cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Great Cottage” I spent a weekend in this cottage and had an overall excellent experience. It is in a great location and is within a close trip to the beach. The cottage was clean, comfortable, and has enough rooms and beds for many people. I will definitely come back next time I am in the Cape.

Responds fast! avg. 3 hours 27 minutes

1 of 2 match: Private outdoor pool (unheated), Wheelchair accessible

1 of 2 filters match

Price per night from

$333

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rentals in Southwest Harbor

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