Winter Harbor Rentals

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101 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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Price per night from

$315

Great rentals within 20 miles that match your search

Unique Yurts Minutes from Acadia National Park

Tremont lodge

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$456

Unique, Secluded Home with Pool: Acadia High Tower

Mount Desert house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$870

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$315

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$195

Starboard Cottage -Spacious cottage overlooking the serene Somes Sound. Located

Mount Desert house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$420

Rockbilt Vista--Newly constructed luxury wing of the Rockbilt Estate

Bar Harbor villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$1,049

Port - an elegant water-view condo in Southwest Harbor

Southwest Harbor condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$248

Pinelodge Cottage - rustic beauty oceanfront near ANP

Bernard cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$561

Harbor Daze - water views in Southwest Harbor

Southwest Harbor chalet

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$263

Jibe Ho- lovely comfortable cottage is the perfect haven for the sailor or natu

Mount Desert house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$263

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$300

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$360

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$510

Midships - modern water-view condo in Southwest Harbor

Southwest Harbor condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$263

Haiku House - your gateway to Acadia

Acadia National Park cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$544

Secluded Home-COTTAGE AT OTTER CREEK-Sleeps 9!

Otter Creek house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

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$258

Idyllic Suite, Ocean and Island Views near Acadia

Southwest Harbor apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$162

Prud'homme Cottage: architect-designed, bright, private cottage on Cove

Bernard cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$413

Eden Villa

Bar Harbor house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 9

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$737

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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$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.

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Price per night from

$229

Virginia's Sunset at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$153

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$298

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.

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$136

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!

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$303

Acorn Cottage

Bar Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$327

Aldernest Cottage (Loft) "quiet" side of Mount Desert Island/Acadia Nat'l Park

Southwest Harbor apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$180

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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Price per night from

$279

Pauls Cottage @ Seaside Cottages, Mt Desert Acadia

Southwest Harbor cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$393

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

Gouldsboro log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$172

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Birch Harbor boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$1,031

Sweet Fern - lovely brand new 2018 apartment in Bar Harbor

Bar Harbor apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$300

Bar Harbor Getaway

Bar Harbor house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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$229

Big Dragonfly - cozy and quaint in the village of Bar Harbor

Bar Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$188

Acadia Dreamscape - quiet & private, near Acadia National Park

Southwest Harbor house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$142

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

Southwest Harbor cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$573

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