Winter Harbor Rentals

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106 Houses

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!!!

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$315

Great rentals within 20 miles that match your search

Idyllic Suite, Ocean and Island Views near Acadia

Southwest Harbor apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$161

The Carriage House in Downtown Bar Harbor! Holland Ave Vacation Rentals!

Bar Harbor house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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$400

Haiku House - your gateway to Acadia

Acadia National Park cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$542

Eden Villa

Bar Harbor house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 9

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$734

Virginia's Sunset at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$152

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$297

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

Southwest Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$262

Aldernest Den-Quiet Side of Mount Desert Island/Acadia - short walk to the shore

Southwest Harbor apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$180

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

Mount Desert cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$278

Pauls Cottage @ Seaside Cottages, Mt Desert Acadia

Southwest Harbor cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$392

Pristine oceanfront cottage

Milbridge cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$294

Captain's Quarters at Captain Bennis House

Sullivan apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

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$114

Annie's Outlook at Sunset Cottages

Acadia National Park cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Great location, beautiful view, cosy place” We visited for a week with our kids (9, 12 years) in July, I can only support my Co-reviewers: a most beautiful location, the sea at your feet, a spectacular sight with sunsets and rocks for kids to climb, with love, taste and insight prepared surroundings (find a bench/picknic table at the places you like to sit), a cosy, clean place, with all you need to feel comfortable, kind people meeting your needs/wishes whereever possible, lots of interesting things to do (hikes, biking, whale watching) in close distance.

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$185

Return to Beauty

Bar Harbor house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$1,084

Perfect Downtown Bar Harbor Location Holland Ave Vacation Rentals

Bar Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$400

Downtown Bar Harbor Near Ocean - Holland Ave Vacation Rentals

Bar Harbor house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

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$297

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

Southwest Harbor cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$571

Deer Track, Cabin Overlooking Somes Sound

Mount Desert house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$245

Cozy Home in Bar Harbor - Acadia in your Backyard

Bar Harbor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$223

Summertime -- Your Home in Bar Harbor

Bar Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$337

20ft. Lofted Ceilings Facing Acadia National Park

Hulls Cove house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$337

Hidden Gem in Bar Harbor - Acadia is your Backyard

Hulls Cove house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$238

SUMMERTIME COTTAGES BAR HARBOR

Hulls Cove house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$799

Kinfolk Cottage

Southwest Harbor house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$400

Lucky Stone Retreat - private beach & Acadia view

Sullivan house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$120

Brookhouse: A Cottage by the Sea

Prospect Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$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.

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$229

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.

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$401

Cristol Cottage - waterfront on Long Pond

Mount Desert cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$315

Pinelodge Cottage - rustic beauty oceanfront near ANP

Bernard cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$561

Anchorage - Harborfront in Southwest Harbor

Southwest Harbor cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“quiet, relaxed and restful, but fun” The location on the quiet side of the island was great. Fun to visit the lobster house, and car museum. Close enough for access to national park, Bar Harbour and nearby attractions. Acadia is obviously unique and beautiful. Location provides good privacy with good access.

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$330

Cedar Ledge & Apt - spectacular views overlooking Frenchmans Bay in Bar Harbor

Bar Harbor cottage

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

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$728

Ledgewood Cottage - large & comfortable near Long Pond & Acadia

Lamoine cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$420

Cole Cottage - waterfront chalet-style 2BR, weekly or monthly near Bar Harbor

Bar Harbor chalet

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

“We had a moose in our front yard!!” We had a wonderful stay at Cole Cottage...topped off by coming home to a very large moose in our front yard that trotted in front of our truck...that was absolutely amazing, still talking about that big boy!! The house is very conveniently located, easy driving to different locations, easy access to acadia Park. The staff at acadia Cotage Rentals couldn't have been more friendly or helpful...my husband left a pillow behind that he uses for back pain. I contacted acadia Cottage Rentals and we had the pillow back within 3 days!! house is situated on lovely Frenchman's Bay, with breathtaking sunsets and sunrises...wonderful beach with a sandbar far into the water, amazing rocks to climb and explore. The house is a little dated, needs some updating...I would strongly suggest redesigning the stairs to the basement, they are a little treacherous! Might also consider turning the 2 basement bedrooms into one big bedroom, and elevate the ceilings so they would be more usable. Other than that, we had an amazing time and loved our trip. Would definitely come back.

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Price per night from

$360

Seal Rock - crafted cabin on the water near Acadia and Bar Harbor

Mount Desert log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$226

Bayside Road - Cozy cottage overlooking Union River Bay

Trenton cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$173

Long Pond View - high-end elegance overlooking Long Pond

Mount Desert house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$710

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