Vacation Rentals & Cottages in Southwest Harbor

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79 cottages

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

Falmouth house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Walking trips

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Price per night from

$688

The Point, Where the Land Meets the Sea

Harpswell house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated) Walking trips

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Price per night from

$918

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Seaside Rosehip Cottage Downeast Maine

Jonesport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$259

Unique Yurts Minutes from Acadia National Park

Tremont lodge

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$454

Welcome to Pleasant Cove in Beautiful Boothbay Maine

Boothbay house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$327

Unique, Secluded Home with Pool: Acadia High Tower

Mount Desert house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$867

Beach Getaway

Moody cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Walking trips, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Responds fast! avg. 1 hour 52 minutes

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$362

Ocean Front Cottage on Penobscot Bay

Belfast cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$322

Working Lighthouse on Picturesque Island in Maine

Saint George lighthouse

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$1,721

Waterfront Home on Scenic Cove

Harpswell house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$184

Classic Oceanfront Cottage on Orr's Island

Orrs Island cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$320

Salt Water Farm,The Studio, Waterfront Organic

Brooksville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$170

Idyllic Suite, Ocean and Island Views near Acadia

Southwest Harbor apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$162

Quintessential Rustic Maine Oceanfront Cottage with Sunset Views

Tremont cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$345

CAMDEN / SPRUCE HEAD SHORE FRONT COTTAGE/HOUSE

Camden house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$211

Pleasant Street Village Home

Vinalhaven house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$281

Very Private 4 bedroom home on 4 Lake Wassookeag

Dexter house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$402

ACADIA National Park. Walk to Ocean, Restaurants! Private Deck Mountain VIEW

Winter Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Comfy and Clean” Our family of five just returned from staying five nights in Winter Harbor. The stay was wonderful and the house was really great. We all felt so at home. The house was spotlessly clean. The neighborhood was very friendly. The owner provided so much helpful information on area sights and restaurants. There was everything we could possible need in the house for cooking. Three bedrooms upstairs provided nice privacy for early risers to start their day without bothering the others. Nice little deck for quiet reading in the sun. Short bike ride to Grindstone Neck. Could have easily biked to Schoodic Point but ended up driving. Just loved it. Hope we can go back again!!!

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$316

Haiku House - your gateway to Acadia

Acadia National Park cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$544

34 Pleasant Street Lubec, ME

Lubec cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$281

Tranquility on Penobscot Bay Private Retreat: Perfect Midcoast/DownEast Location

Stockton Springs house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 42 minutes

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$345

Cozy 1 bedroom house in Rockport Village

Rockport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$144

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: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$303

Minutes from Popham Beach - Cozy Maine Coast Cottage

Phippsburg cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$259

Oceanfront Cottage w/ Dock & Mooring - walking distance to Acadia

Southwest Harbor cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$574

Fundy Seashore Beach House

Chance Harbour house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 19 minutes

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$143

Reunion Grove Farm - Relax with us!

Warren farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$218

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$918

Cozy Keyes Cottage

East Winthrop house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$482

MoonLight Treehouse

Belgrade tree house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$802

Little Landing Cottage

East Winthrop cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$516

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$471

Bear Mountain Lodge - 560 Acres of Private Estate

Robbinston house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$286

"Tugwassa" On Down East Jones Pond- poet's cottage

Gouldsboro log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$172

Maine. Lovely Cottage on Penobscot Bay

Penobscot cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“Amazingly well equipped and idylically located.” Everything you could want in a vacation cottage except a beach. Great for a poet or a painter. Not a lot of action in the immediate neighborhood, but not far away.Quiet, well maintained and comfortable.

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$244

Bar Harbor Getaway

Bar Harbor house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$230

1 of 2 match: Shared outdoor pool (heated), Walking trips

1 of 2 filters match

Price per night from

$207

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rentals in Southwest Harbor

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