Vacation Rentals & Cottages in Southwest Harbor

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341 cottages

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New Castle chateau

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Shared outdoor pool (unheated) Beach or lakeside relaxation

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Price per night from

$652

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Price per night from

$200

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Private Safe Beach Community

Hampton apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$571

iDream beautiful place by the sea

Ogunquit house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$652

Finch Cottage

New Harbor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“A very enjoyable stay in New Harbor” The Fletchers went out of their way to ensure that we had a good stay at the Finch Cottage. They provided detailed information on things to do and restaurants in the area. They also asked our specific interests and provided information geared especially to us. The cottage met our needs very well. It was quaint and cozy but with all the modern amenities, including Wi-Fi. The kitchen was well stocked and most things provided.

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$143

Great Location - Waterview Apartment

Old Orchard Beach apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

“Five Stars Plus” An excellent weeks stay in Old Orchard Beach. Our rental stay was great. Clean and comfortable for our group of 7. Close to beach and quiet, yet close enough to enjoy the downtown action.

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$206

Home away from Home

Hampton condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$278

Single Family Home minutes from the beach

Old Orchard Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Pleasant stay at Old Orchard Beach” Great place to stay with kids, nice yard and deck. I like that it's away from the noise and congestion but still has nearby restaurants to walk to . Had a very pleasant stay.

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$160

Sunshine House steps from Beach

Seabrook house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$799

Hillside Ocean View 2BR with Private Beach Access

Ipswich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$189

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$400

Family House on Short Sands at York Beach

York Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$400

Cliffside at Sandcliff by the Sea

Bar Harbor house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“We had a great vacation experience at Cliffside..” We had a marvelous time during our stay at Cliffside and thoroughly enjoyed our trip and the use of this beautiful home with our friends. It was a great location-close to the park and town, but nestled amongst the trees for relaxing privacy. We saw deer behind the house several mornings and took some great pictures of a hawk perched in the tree just beyond our deck. The trails behind the house and Sand Point Road were convenient for morning hiking and jogging. Several mornings we enjoyed our coffee on the decks with their peaceful views of the bay. This lovely home provided a great base for visiting Bar Harbor and acadia- whale watching, visits to Cadillac Mountain, Sand Beach, Thunder Hole, and the Thuya Gardens. We hiked around Jordan Pond and enjoyed the tea and popovers, visited Schoodic Peninsula, and took a carriage tour of the bridges. We really appreciated Bonnie's suggestions for dining and activities to enjoy, and everything went very smoothly from beginning to end. The weather was great and we had a wonderful time.

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$424

9 Perio Point

Beals house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$237

Private Island - Great for Reunions - Sleeps 24

Port Clyde house

  • 11 bedrooms
  • 6 bathrooms
  • sleeps 24

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$2,444

Summer Rental - Marguerite- Biddeford Pool ME

Biddeford Pool cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$490

West Lee Cottage

Swans Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 46 minutes

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$183

Virginia's Sunset at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$152

Cedarledge Cottage at Seaside Cottages, waterfront, Acadia - "quiet" side of MDI

Southwest Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$262

Waterfront Cottage, Stroll Away from Historic Bath

Bath cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$319

Maine Ocean Front 2 Bedroom Cottage

Tenants Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“A Little Bit of Heaven” Several years ago I had the good fortune to rent this cottage "sight unseen" and have been returning each year for 10 or so years which tells you how much I love it here. Dream about it in the winter too. It is immaculate, close to a small beach, stores, and not too far from Rockland and Camden. If I could, I would spend the summer here and be in heaven! Tranquil, beautiful, soothing and good for the soul are some of the ways I would describe Hupper Cottage. The owners are terrific and most accommodating. In my opinion you won't find a better place to stay in Maine for rest and relaxation! Walking and sight seeing are great, and the lobster and sunsets are fabulous! Great hub for sightseeing in mid-coast Maine as well.

Responds fast! avg. 2 hours 24 minutes

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$160

Pinelodge Cottage, Quiet side of Mt. Desert Island, Acadia Natl.Park, waterfront

Mount Desert cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$278

Pauls Cottage @ Seaside Cottages, Mt Desert Acadia

Southwest Harbor cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$392

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: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$268

Waterfront villa, Coastal Southern Maine

Scarborough house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$1,141

Quaint Cottage

Wytopitlock cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$14

Ogunquit Condo - 5 Minute Walk to Footbridge Beach!

Ogunquit condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$200

Great Price, Classy, Fully Furnished 1-bedroom Apt. in a House

Portsmouth apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$399

SeaShine Getaway

Ogunquit condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$205

Seaside Rosehip Cottage Downeast Maine

Jonesport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$257

Rustic, Romantic, & Spacious Log Chalet BEST PLACE for Family, & Friends

Cape Neddick chalet

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$873

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$286

Maine Bed & Boat, MAZU

Damariscotta yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$337

Grace Cottage

Long Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$411

Heart of North Conway/ three level Condo

North Conway apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$229

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: Shared outdoor pool (unheated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$135

Brookhouse: A Cottage by the Sea

Prospect Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$195

The Gray Barn

Bass Harbor apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Close to Nirvana” It would be difficult to find a better spot for spending a vacation than the Quietside of Mt. Desert, and the Gray Barn experience is part of the fun. The accomodations are modern and in great shape, and the windows both have a great view over upper Bass Harbor and give great air circulation. Access to cellphone and internet coverage is a convenience. The kitchen is very functional, though you'll want to visit the lobster pounds and restaurants in the area. A perfect base for hiking in acadia National Park. The week we were there was perfect for using the owner's kayaks in the upper harbor and the estuary beyond. We've stayed three different years and will be happy to return.

1 of 2 match: Shared outdoor pool (unheated), Beach or lakeside relaxation

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Price per night from

$229

Viewing 38 of 341
rentals in Southwest Harbor

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