Vacation Rentals & Cottages in Southwest Harbor

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35 cottages

Maine Bed & Boat, MAZU

Damariscotta yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Boat available Solarium or roof terrace

All filters match

Price per night from

$338

Maine Bed & Boat, NEBI

Damariscotta boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Boat available Solarium or roof terrace

All filters match

Price per night from

$338

These homes match some but not all of your filters. Clear all filters

Primitive cabin on Penobscot River.

Milford house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$82

Cozy 1 bedroom house in Rockport Village

Rockport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$144

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$126

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: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$245

Family Friendly Cottage on Androscoggin Lake

Leeds cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Solarium or roof terrace, 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: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$2,453

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: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$270

Pristine oceanfront cottage

Milbridge cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$295

Tidewater Popham Beach House

Phippsburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Solarium or roof terrace

1 of 2 filters match

Price per night from

$457

34 Pleasant Street Lubec, ME

Lubec cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Boat available, Solarium or roof terrace

1 of 2 filters match

Price per night from

$281

SUMMER COTTAGE BY THE SEA

Swans Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$286

Farm Stay Cottage @ Toddy Pond Farm

Belfast house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$298

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: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$230

West Lee Cottage

Swans Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 46 minutes

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$184

Rustic Lakeside Lodge and Four Cabins-13 bedrooms

Jefferson lodge

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 26

1 of 2 match: Solarium or roof terrace, 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: Solarium or roof terrace, 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: Solarium or roof terrace, 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: Solarium or roof terrace, 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: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$115

Star Point on Snow Pond in the Belgrade Lakes

Belgrade cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$377

Reunion Grove Farm - Relax with us!

Warren farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$217

Tiny House Cottage

Boothbay Harbor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$172

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

Bernard cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Solarium or roof terrace, 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: Solarium or roof terrace, 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: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$797

Center Pond Retreat

Sangerville log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$180

1 of 2 match: Solarium or roof terrace, 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: Solarium or roof terrace, 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: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$172

Private Sandy Beach, Sleeps 24+ large family's, Retreats and Weddings 5 star

Sandy Point house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 21

Responds fast! avg. 3 hours 12 minutes

1 of 2 match: Boat available, Solarium or roof terrace

1 of 2 filters match

Price per night from

$800

Coastal Mountains Stunning Mountain & Ocean View

Rockport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Solarium or roof terrace

1 of 2 filters match

Price per night from

$516

The Point, Where the Land Meets the Sea

Harpswell house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$914

Lakefront Trifecta with Hot Tub!

Augusta house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Solarium or roof terrace, Boat available

1 of 2 filters match

Price per night from

$228

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