Vacation Rentals & Cottages in Southwest Harbor

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33 cottages

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".

Match: Boat available Climbing frame

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Price per night from

$269

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Primitive cabin on Penobscot River.

Milford house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$82

Beautiful new house + classic cottage Seal Harbor

Seal Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Boat available, Climbing frame

1 of 2 filters match

Price per night from

$916

Ocean View Cape on 14 Private Acres

Searsport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Climbing frame

1 of 2 filters match

Price per night from

$373

Cozy 1 bedroom house in Rockport Village

Rockport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$144

Family Friendly Cottage on Androscoggin Lake

Leeds cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$344

Private Island - Great for Reunions - Sleeps 24

Port Clyde house

  • 11 bedrooms
  • 6 bathrooms
  • sleeps 24

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$2,453

Pristine oceanfront cottage

Milbridge cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$295

Moose Tracks

Lincolnville cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“Wonderful” My family and I spent a week at Moose Tracks and we had a fantastic time! We couldn't have asked for better weather, and the lake was absolutely beautiful. We hope to come back next summer!

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$245

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$126

Maine Bed & Boat, NEBI

Damariscotta boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$338

The Gray Barn

Bass Harbor apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Close to Nirvana” It would be difficult to find a better spot for spending a vacation than the Quietside of Mt. Desert, and the Gray Barn experience is part of the fun. The accomodations are modern and in great shape, and the windows both have a great view over upper Bass Harbor and give great air circulation. Access to cellphone and internet coverage is a convenience. The kitchen is very functional, though you'll want to visit the lobster pounds and restaurants in the area. A perfect base for hiking in acadia National Park. The week we were there was perfect for using the owner's kayaks in the upper harbor and the estuary beyond. We've stayed three different years and will be happy to return.

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$229

West Lee Cottage

Swans Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 46 minutes

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$184

Maine Bed & Boat, MAZU

Damariscotta yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$338

Rustic Lakeside Lodge and Four Cabins-13 bedrooms

Jefferson lodge

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 26

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$1,211

Waterfront vacation home--fully equipped

Liberty house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$376

Midcoast Waterfront Maine Home- Direct Waterfront, secluded site.

Cushing house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$311

lakefront chalet style house on sebec lake

Sebec chalet

  • 1 bedroom
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$401

Lakeside Cabin Near Belfast Bay w/ Kayaks & Canoe

Swanville log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$115

Farm Stay Cottage @ Toddy Pond Farm

Belfast house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$298

SUMMER COTTAGE BY THE SEA

Swans Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$287

Prud'homme Cottage: architect-designed, bright, private cottage on Cove

Bernard cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$413

Oceanfront Cottage On Linekin Bay Boothbay Harbor

Boothbay Harbor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$287

Breezeway Cottage

Lincolnville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$796

Center Pond Retreat

Sangerville log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$180

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$298

Lake Front Maine Cabin on Cold Stream Pond

Burlington log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$229

"Tugwassa" On Down East Jones Pond- poet's cottage

Gouldsboro log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$172

Star Point on Snow Pond in the Belgrade Lakes

Belgrade cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$378

Tiny House Cottage

Boothbay Harbor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$172

Reunion Grove Farm - Relax with us!

Warren farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$218

Lakefront Trifecta with Hot Tub!

Augusta house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$228

The Point, Where the Land Meets the Sea

Harpswell house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Climbing frame, Boat available

1 of 2 filters match

Price per night from

$916

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