Vacation Rentals & Cottages in Southwest Harbor

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41 cottages

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New Castle chateau

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Children's pool Golf course on site or within 15 min walk

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Price per night from

$657

Match: Children's pool Golf course on site or within 15 min walk

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Price per night from

$202

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Spacious 5 Bedroom vacation house in the Heart of North Conway

North Conway house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 16

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$689

Cottage On The Green - On golf course & near beach

Kennebunk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$526

Great Location! Best Prices! 5th house to Beach

Old Orchard Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$173

Seal Cove Beach Smokeshed Cottages

Grand Manan house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$115

92 Locust Lane

North Conway house

  • 16 bedrooms
  • 11 bathrooms
  • sleeps 34

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$2,990

80 Locust Lane

North Conway house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$1,208

42 Locust Lane

North Conway house

  • 10 bedrooms
  • 5 bathrooms
  • sleeps 20

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$1,955

70 Locust Lane

North Conway house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$1,058

Spectacular White Mountain Home Getaway

North Conway house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$460

Linderhof - 2 bedroom condo

Glen condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$156

10 Locust Lane

North Conway house

  • 15 bedrooms
  • 9 bathrooms
  • sleeps 32

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$2,760

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: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$133

Linderhof Golf Course Condo / Across from Storyland

Glen condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

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Price per night from

$229

ON MOUNTAIN, SKI IN-SKI OUT Sleeps 14-16 HappyTrails

Newry house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 58 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$1,604

3 Bedroom 2 Bath Association beach

Moultonborough house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$361

OCEAN COTTAGE - Beachfront property w/ water views - 2 private decks & beach

Northport cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$317

Locke Lake Waterfront Property

Center Barnstead house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$395

Log Cabin in the Best Town on Mt. Desert Island

Southwest Harbor log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“This is very clean, well-accomodated, and in a great location!” Our family just returned from a week in this great cabin. We wanted to be very close to acadia National Park, but not in a busy area. The location was perfect for this. The cabin is within walking distance of a small town with great restaurants and stores, and a very short drive (some 5 minutes, some 10 minutes, some 15 minutes) to all the sights of the national park. And when you return to the cabin you experience its quiet and natural setting at its best. It was rejuvenating to be there. The owners have obviously taken a lot of time and effort to make their home user-friendly. It comes equipped with everything you need for cooking and relaxing. Everything is clean and cared for, and the entire cabin has a cozy yet spacious feel to it. Very highly recommended!

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$304

Bar Harbor Getaway

Bar Harbor house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$230

Tiny House Cottage

Boothbay Harbor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$173

Beach Getaway

Moody cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Children's pool

1 of 2 filters match

Price per night from

$288

The Pickering House - an 1854 Harbor View Home

Deer Isle farmhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$460

Perfect Location & Best Prices! 5th house to beach

Old Orchard Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$190

Bayview Cottage

Welshpool house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$207

Very Private Family Compound on Lake Winnisquam

Belmont villa

  • 10 bedrooms
  • 4 bathrooms
  • sleeps 25

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$2,054

Maple View House: fireplaces, sauna, jettub, 4 TVs, deck, firepit, game room, AC

North Conway house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 19

Responds fast! avg. 12 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$460

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$690

Comfy Seaside Cabana

Hunts Point villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 55 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$378

Shawnee Peak - Ski In & Out - 3 Bedroom

Bridgton ski chalet

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$920

Beautiful Log Cabin on Belleau Lake - Pet Friendly, Beach, Kayaks- 2900 sqft!

East Wakefield log cabin

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$403

Warm and cozy Waterville Valley condo on x-ski trail

Waterville Valley townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$230

Oceanfront Cottage On Linekin Bay Boothbay Harbor

Boothbay Harbor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$288

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft, 100ft Beachfront, Kayaks, Dock

East Wakefield house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$863

Picture Perfect Home so close to Cannon Mountain_Franconia Notch!

Franconia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$248

Pine Brook Lodge: 3 fireplaces, sauna, game room, bar, 4 TVs, AC, deck, grill

North Conway house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 12 minutes

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$368

Andy's Retreat - Heated outdoor pool, Hot Spring jacuzzi, central AC, BBQ

Falmouth house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$689

Viewing 38 of 41
rentals in Southwest Harbor

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