Vacation Rentals & Cottages in Southwest Harbor

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Very Private Family Compound on Lake Winnisquam

Belmont villa

  • 10 bedrooms
  • 4 bathrooms
  • sleeps 25

Responds fast! avg. 1 hour 4 minutes

Match: Boat available Wheelchair accessible

All filters match

Price per night from

$2,045

The Farm at Worthley Pond, Private Beach & Wedding Barn

Peru house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 25

Match: Boat available Wheelchair accessible

All filters match

Price per night from

$1,002

Waterfront Real Log Cabin - Gorgeous Lake Francis

Pittsburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 50 minutes

Match: Boat available Wheelchair accessible

All filters match

Price per night from

$286

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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: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$126

Yellow Tuna Hostel - Yellow Tuna

Wedgeport guest house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$364

9 Perio Point

Beals house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$237

house on miles pond

Concord house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 22 minutes

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$144

Whetstone Cottage On The Lake

Abbot Village house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$148

Clean comfortable chalet located in the heart of new Hampshire

Bethlehem house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$263

Unique Yurts Minutes from Acadia National Park

Tremont lodge

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$453

Ledgewood Cottage - large & comfortable near Long Pond & Acadia

Lamoine cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$420

“Privacy and location cannot be beat!” Great home - spread out and quite large - almost too large for the 6 of us! Access to the bay was amazing, easy 5-10 minutes into town and to acadia National park, quiet road; very private location. Pet friendly and cozy enough for movies on the couch for those dastardly rainy days.

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$750

Hampton Beach, Beachfront Condominium

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$287

Ocean Front Condo on Hampton Beach

Hampton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$328

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$666

Beachfront Cottage on Indian Point

Georgetown cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$315

Greenville Log Cabin w/ Bunkhouse

Greenville log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 11

“Excellent stay” the location is amazing the beach is on the doorstep this is a great family pet friendly caven We ll visit again

Responds fast! avg. 2 hours 39 minutes

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$172

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$400

Bayside Road - Cozy cottage overlooking Union River Bay

Trenton cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$173

Cristol Cottage - waterfront on Long Pond

Mount Desert cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$315

cozy oceanfront cottage

Hancock cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 47 minutes

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$196

Spacious 1 bedroom condo near 5 major ski areas!

Glen condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 1 hour 47 minutes

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$132

Enjoy Spectacular Views of Lake and Loon Mountain

Lincoln condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$229

Primitive cabin on Penobscot River.

Milford house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$82

“Surf View” - Oceanfront

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$344

Clean and Cozy Oceanfront Condo

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Wheelchair accessible

1 of 2 filters match

Price per night from

$287

Charming Early 1900s Lakeside Cottage

Rangeley house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$229

Cozy 1 bedroom house in Rockport Village

Rockport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$144

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: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$245

Private Island - Great for Reunions - Sleeps 24

Port Clyde house

  • 11 bedrooms
  • 6 bathrooms
  • sleeps 24

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$2,453

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: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$115

Pristine oceanfront cottage

Milbridge cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$295

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$126

Taffy Lake Retreat

Nackawic log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$172

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: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$269

Maine Lakefront Cottage on Moose Pond, Denmark

Denmark cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$287

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$195

Family Friendly Cottage on Androscoggin Lake

Leeds cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Wheelchair accessible, Boat available

1 of 2 filters match

Price per night from

$344

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