Vacation Rentals & Cottages in Southwest Harbor

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265 cottages

Slice of Paradise at Hampton Beach, NH

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (heated) Beach or lakeside relaxation

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Price per night from

$269

Relaxing Oceanfront Retreat

Hunts Point house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 56 minutes

Match: Private outdoor pool (heated) Beach or lakeside relaxation

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Price per night from

$1,045

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Private Safe Beach Community

Hampton apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$573

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: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$161

iDream beautiful place by the sea

Ogunquit house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$654

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: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$144

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: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$206

Hillside Ocean View 2BR with Private Beach Access

Ipswich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$189

Home away from Home

Hampton condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$279

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$401

Sunshine House steps from Beach

Seabrook house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$802

Reservations

New Castle chateau

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$654

Family House on Short Sands at York Beach

York Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$401

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: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$425

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: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$229

9 Perio Point

Beals house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (heated), 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: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$2,453

Heart of North Conway/ three level Condo

North Conway apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$229

Summer Rental - Marguerite- Biddeford Pool ME

Biddeford Pool cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$492

West Lee Cottage

Swans Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 46 minutes

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$184

Maine Bed & Boat, MAZU

Damariscotta yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$338

Brookhouse: A Cottage by the Sea

Prospect Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$196

Virginia's Sunset at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$153

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

Southwest Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$263

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: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$136

Waterfront Cottage, Stroll Away from Historic Bath

Bath cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

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Price per night from

$320

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: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$161

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: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$279

Pauls Cottage @ Seaside Cottages, Mt Desert Acadia

Southwest Harbor cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$393

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: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$269

Waterfront villa, Coastal Southern Maine

Scarborough house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$1,145

Quaint Cottage

Wytopitlock cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

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: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$201

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

Portsmouth apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$400

SeaShine Getaway

Ogunquit condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), 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: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$258

Grace Cottage

Long Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$413

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

Cape Neddick chalet

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (heated), Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$876

Viewing 38 of 265
rentals in Southwest Harbor

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