Vacation Rentals & Cottages in Southwest Harbor

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98 cottages

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".

Match: Climbing frame Beach or lakeside relaxation

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Price per night from

$269

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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: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$144

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$287

Seaside Rosehip Cottage Downeast Maine

Jonesport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Beach or lakeside relaxation

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Price per night from

$258

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: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$401

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: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$229

9 Perio Point

Beals house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

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: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$2,453

West Lee Cottage

Swans Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 46 minutes

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$184

Maine Bed & Boat, MAZU

Damariscotta yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$338

Brookhouse: A Cottage by the Sea

Prospect Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$196

Virginia's Sunset at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

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: Climbing frame, 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: Climbing frame, 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: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

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: Climbing frame, 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: Climbing frame, 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: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$393

Grace Cottage

Long Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$413

Beautiful new house + classic cottage Seal Harbor

Seal Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Beach or lakeside relaxation, Climbing frame

1 of 2 filters match

Price per night from

$916

Ocean View Cape on 14 Private Acres

Searsport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Beach or lakeside relaxation, Climbing frame

1 of 2 filters match

Price per night from

$373

Sunset Chalet

Belgrade chalet

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$573

SkyView treehouse

Belgrade tree house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$686

Kendall Farm Cottages

Perry cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$196

Family Friendly Cottage on Androscoggin Lake

Leeds cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$344

Center Pond Retreat

Sangerville log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$180

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$298

Bay of Fundy Seaside Cottage

Chance Harbour cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 16 minutes

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$155

Maine Cottage, Mid-Coast Maine

South Bristol cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$161

Responds fast! avg. 1 hour 52 minutes

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$361

Rustic Lakeside Lodge and Four Cabins-13 bedrooms

Jefferson lodge

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 26

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$1,211

Ocean Front Cottage on Penobscot Bay

Belfast cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$321

Salt Water Farm,The Studio, Waterfront Organic

Brooksville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$170

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$126

Beautiful Seaside Island Home

Long Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$458

Very Private 4 bedroom home on 4 Lake Wassookeag

Dexter house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$401

Lakefront Trifecta with Hot Tub!

Augusta house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$228

1 of 2 match: Climbing frame, Beach or lakeside relaxation

1 of 2 filters match

Price per night from

$189

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rentals in Southwest Harbor

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