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

Match: Safe Staffed property

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Price per night from

$2,049

Unique A-Frame Working Farmhouse in Maine

Rumford b&b

  • 3 bedrooms
  • 1 bathroom
  • sleeps 10

Match: Safe Staffed property

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Price per night from

$144

Unique A-Frame Farmhouse on Working Farm in Maine

Rumford farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Safe Staffed property

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Price per night from

$230

Match: Safe Staffed property

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Price per night from

$81

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"DISCOUNTED PRICE FOR ANY WEEK IN JUNE" Townhouse in Ocean Park Meadows, OOB

Old Orchard Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Safe, Staffed property

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Price per night from

$292

The Mission House Bed & Breakfast - a beautiful, historic property

Gagetown b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Safe, Staffed property

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Price per night from

$109

1 of 2 match: Safe, Staffed property

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Price per night from

$197

Campground/RV Park,Tenting,Day camping,Swimming,Full Service to Rustic sites

Fredericton cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 9

1 of 2 match: Staffed property, Safe

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Price per night from

$80

Unique Two-Story Log Cabin on Special Lake - no motors

Rangeley house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Staffed property, Safe

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Price per night from

$253

1 of 2 match: Staffed property, Safe

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Price per night from

$101

Annie's Outlook at Sunset Cottages

Acadia National Park cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Great location, beautiful view, cosy place” We visited for a week with our kids (9, 12 years) in July, I can only support my Co-reviewers: a most beautiful location, the sea at your feet, a spectacular sight with sunsets and rocks for kids to climb, with love, taste and insight prepared surroundings (find a bench/picknic table at the places you like to sit), a cosy, clean place, with all you need to feel comfortable, kind people meeting your needs/wishes whereever possible, lots of interesting things to do (hikes, biking, whale watching) in close distance.

1 of 2 match: Safe, Staffed property

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Price per night from

$186

Relaxing And Clean - Maine Seacoast

Kittery house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Safe, Staffed property

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Price per night from

$157

Little Cottage at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Peaceful, Romantic and Inspiring” First I must say that all folks involved in the rental and care of the cottages are the tops. They know just how to be there for everything you might need without being intrusive, and the cottage is very bright and clean. This small cottage is on one spectacular piece of property where we sat by the cove each night in strategically placed adirondack chairs to watch the glorious sunsets. Cannot recommend Little Cottage too highly for a couple or single, as long as they are not too tall. The location is perfect for those who want to be on the quiet side.

1 of 2 match: Safe, Staffed property

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Price per night from

$136

STRONG TIMBERS B AND B CRICKET HOLLOW

Kingsclear b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Safe, Staffed property

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Price per night from

$118

Beachfront Condo with Great Views

Old Orchard Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Safe, Staffed property

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Price per night from

$253

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: Safe, Staffed property

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Price per night from

$127

Virginia's Sunset at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Safe, Staffed property

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Price per night from

$153

Green Edge Of Fabulous Downtown

Portsmouth apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Safe, Staffed property

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Price per night from

$630

The 1760 Tavern, Charming Antique Colonial

Townsend manor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Staffed property

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Price per night from

$206

Getaway To Silence , Artsy Forested Woodland Home

Parsonsfield house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Safe, Staffed property

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Price per night from

$505

1 of 2 match: Safe, Staffed property

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Price per night from

$155

Oceanfront Cottage On Linekin Bay Boothbay Harbor

Boothbay Harbor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Safe, Staffed property

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Price per night from

$287

Tiny House Cottage

Boothbay Harbor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Safe, Staffed property

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Price per night from

$172

Secluded Home-COTTAGE AT OTTER CREEK-Sleeps 9!

Otter Creek house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Safe, Staffed property

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Price per night from

$258

Hillside Ocean View 2BR with Private Beach Access

Ipswich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Safe, Staffed property

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Price per night from

$189

Rust Pond Camp at Grey Shingles Camps

Wolfeboro cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Safe, Staffed property

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Price per night from

$292

Comfy Seaside Cabana

Hunts Point villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 56 minutes

1 of 2 match: Safe, Staffed property

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Price per night from

$376

Cozy 1 bedroom house in Rockport Village

Rockport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Staffed property, Safe

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Price per night from

$144

Downtown "Namastay"

Rockland house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Staffed property, Safe

1 of 2 filters match

Price per night from

$431

Black Bear Pond Cabins

Patten guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Staffed property, Safe

1 of 2 filters match

Price per night from

$228

Big Red House - Historic Bangor Home

Bangor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Staffed property, Safe

1 of 2 filters match

Price per night from

$281

Slopeside Attitash near StoryLand, White Mountains

Glen condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Safe, Staffed property

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Price per night from

$230

The Point, Where the Land Meets the Sea

Harpswell house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Safe, Staffed property

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Price per night from

$918

1 of 2 match: Safe, Staffed property

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Price per night from

$401

BEACH RENTAL WITH 3 BEDROOMS,A/C & FREE BEACHFRONT PARKING

Old Orchard Beach apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 10

1 of 2 match: Staffed property, Safe

1 of 2 filters match

Price per night from

$410

Private Lakefront Cottage on a Unique Setting - Maine At It's Best!

Limerick house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Staffed property, Safe

1 of 2 filters match

Price per night from

$181

Brand New Modern Loft Home

Topsham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Safe

1 of 2 filters match

Price per night from

$213

Captain's Quarters at Captain Bennis House

Sullivan apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

1 of 2 match: Staffed property, Safe

1 of 2 filters match

Price per night from

$115

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rentals in Southwest Harbor

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