Vacation Rentals & Cottages in Southwest Harbor

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New Castle chateau

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$655

Responds fast! avg. 1 hour 4 minutes

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$203

Responds fast! avg. 1 hour 4 minutes

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$243

Responds fast! avg. 1 hour 4 minutes

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$137

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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$82

SKI IN SKI OUT! Luxury Rare Mountainside Unit

Glen condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Boat available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$373

Perfect little Condo

Waterville Valley condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Shared outdoor pool (unheated)

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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$230

Cozy 1 bedroom house in Rockport Village

Rockport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$144

Renovated House Nestled in the White Mountains

Campton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$316

Lake Winni - Condo - 205

Laconia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Boat available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$139

Escape to Ogunquit - a pool, the beach, Perkins Cove and the Footbridge

Ogunquit condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Boat available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$543

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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$246

Private Island - Great for Reunions - Sleeps 24

Port Clyde house

  • 11 bedrooms
  • 6 bathrooms
  • sleeps 24

1 of 2 match: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$2,458

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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$295

Taffy Lake Retreat

Nackawic log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$339

Lake House with over 200 feet of private waterfront beach!

Denmark chalet

  • 5 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$287

Family Friendly Cottage on Androscoggin Lake

Leeds cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$183

1 of 2 match: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$195

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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$115

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$115

1 of 2 match: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$126

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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$2,049

Rustic Lakeside Lodge and Four Cabins-13 bedrooms

Jefferson lodge

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 26

1 of 2 match: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$287

1 of 2 match: Shared outdoor pool (unheated), Boat available

1 of 2 filters match

Price per night from

$499

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rentals in Southwest Harbor

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