Vacation Rentals & Cottages in Southwest Harbor

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Saddleback Mountain On Slopes 3-4BR Ski-in/out Condo Near Rangeley

Rangeley condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Boat available Skiing – property near ski resort

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Price per night from

$401

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Primitive cabin on Penobscot River.

Milford house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, 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: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$144

Charming Early 1900s Lakeside Cottage

Rangeley house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$230

Private Island - Great for Reunions - Sleeps 24

Port Clyde house

  • 11 bedrooms
  • 6 bathrooms
  • sleeps 24

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$2,459

Labor Day Holiday week 9/2-9/9 available! Book Now!

Moultonborough cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 9

“Great spot to unwind and get away from it all !!” Very pleased. My family had a ball. Was there end of august and plan to return next month and next august Rooms are good size, plenty of closet space, and fully equipped Kitchen. Clean and well card for property.

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$115

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: Skiing – property near ski resort, 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: Skiing – property near ski resort, 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: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$246

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$127

Taffy Lake Retreat

Nackawic log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$172

Maine Bed & Boat, NEBI

Damariscotta boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$339

Family Friendly Cottage on Androscoggin Lake

Leeds cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$345

Lakeside cottage with boats,grill &firepit! Family friendly!

Poland cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$183

Lake House with over 200 feet of private waterfront beach!

Denmark chalet

  • 5 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$225

Maine Lakefront Cottage on Moose Pond, Denmark

Denmark cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$287

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$195

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$118

Luney Dunes Penthouse: 1 Dog ok, Ocean View, Deck, Spa Bath, Jetted Tub, Walk to

Newburyport hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$115

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$203

Red House w/ Access to Sebago Cove

Naples house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$393

Beautiful Waterfront Log Cabin - White Mountains

White Mountains house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 9

“Lake cabin” Beautiful location..owner very kind and helpful.Very private..yet close to attractions.The view from the deck is beautiful.

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$431

West Lee Cottage

Swans Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 46 minutes

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$184

Cottage on Halfmoon Lake

Alton cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$222

Very Private Family Compound on Lake Winnisquam

Belmont villa

  • 10 bedrooms
  • 4 bathrooms
  • sleeps 25

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$2,050

Rustic Lakeside Lodge and Four Cabins-13 bedrooms

Jefferson lodge

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 26

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$1,213

Waterfront vacation home--fully equipped

Liberty house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$377

Midcoast Waterfront Maine Home- Direct Waterfront, secluded site.

Cushing house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Skiing – property near ski resort, 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: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$402

Lakeside Cabin Near Belfast Bay w/ Kayaks & Canoe

Swanville log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$115

SUMMER COTTAGE BY THE SEA

Swans Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$287

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$500

Farm Stay Cottage @ Toddy Pond Farm

Belfast house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$299

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: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$230

Maine Bed & Boat, MAZU

Damariscotta yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$338

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$234

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$119

Linden Tree: Walk to Enchanting Downtown, Spacious, Gas Fireplace, Tree Swing, G

Newburyport hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Skiing – property near ski resort, Boat available

1 of 2 filters match

Price per night from

$156

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rentals in Southwest Harbor

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