Vacation Rentals & Cottages in Southwest Harbor

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Wells, Maine Cottage w/Pool, hot tub, Gym & more....

Moody cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Children's pool Kettle

All filters match

Price per night from

$241

Slopeside Attitash near StoryLand, White Mountains

Glen condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Children's pool Kettle

All filters match

Price per night from

$230

Match: Children's pool Kettle

All filters match

Price per night from

$201

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Beach Getaway

Moody cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Kettle, Children's pool

1 of 2 filters match

Price per night from

$287

Village of Winnipesaukee 2br suite, Sunday check-in

Weirs Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Kettle, Children's pool

1 of 2 filters match

Price per night from

$86

Reservations

New Castle chateau

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Kettle, Children's pool

1 of 2 filters match

Price per night from

$655

Barn Camp on Clearwater Lake, Farmington (Industry), Maine

Farmington cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$139

The Fredric 3 Bedroom Apartment With Outside And Free Parking

Portland apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$476

Lake Winni - WF - 428

Meredith house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$11,473

Black Bear Pond Cabins

Patten guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$228

Lake Winni - WF - 373

Center Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$406

Silver Lake - WF - 359

Lochmere house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$335

Silver Lake - WF - 306

Belmont house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$57,249

Lake Winni - BA - 112

Moultonborough house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$57,249

Lake Winni - WF - 305

Tuftonboro house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$348

Lake Winni - BA - 244

Gilford house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$243

Kellie Ann's Breakwater, Oceanfront living

Saco house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$459

Ocean Waterfront - Walk to Pemaquid Light

New Harbor house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$369

Prime Village Location - 5 Minute Walk to Beach!

Ogunquit condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$241

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: Children's pool, Kettle

1 of 2 filters match

Price per night from

$246

Waterfront Cottage, Stroll Away from Historic Bath

Bath cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$320

“Cozy New England Cottage Was Perfect!” It was just a short walk to lobster rolls and nightly entertainment, which was great for unwinding at the end of the night after a tough day at the beach! The neighborhood was nice and quiet, with friendly people and a wonderful atmosphere. It was fantastic to be able to see the Wednesday night fireworks from my back deck! The cottage was comfortable and I felt like I was right at home. Lots of amenities, like aC, cable, and wireless internet!

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$279

Aldernest Den-Quiet Side of Mount Desert Island/Acadia - short walk to the shore

Southwest Harbor apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$181

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

Old Orchard Beach apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 10

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$410

Waterfront Home on Scenic Cove

Harpswell house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$184

Chase Cottage

Dover Foxcroft house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 15

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$345

Quintessential Rustic Maine Oceanfront Cottage with Sunset Views

Tremont cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$345

Comfy A/C Cottage in the OCEAN PARK AREA just 75 yards from the OOB sandy beach!

Old Orchard Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$413

Brand New Modern Loft Home

Topsham house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$213

Edgewater Cottage

Sebec cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$184

Taffy Lake Retreat

Nackawic log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$172

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$195

Linderhof - 2 bedroom condo

Glen condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$155

Rangeley Lakeside Cottage

Rangeley cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$287

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$83

Ellenton Cottage on the Cove, Prospect Harbor

Prospect Harbor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$311

Lynn Ann Cottage with great deck in “Island Section”! Dog friendly!

Hampton cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Just right for a wonderful beach vacation” My husband and I have stayed at this cute little cottage for many years. It is by no means fancy or large, but it is just what is needed for a great little get away every fall. We can bring our family dog with us, and we enjoy drinking our coffee on the gorgeous deck every morning, and taking walks on the beach at sunset. We keep coming back because of the fabulous location and wonderful memories!

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$328

Maine Bed & Boat, NEBI

Damariscotta boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Kettle

1 of 2 filters match

Price per night from

$338

Viewing 38 of 264
rentals in Southwest Harbor

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