Winter Harbor Rentals

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79 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

$316

Great rentals within 20 miles that match your search

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

Bar Harbor house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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$402

Eden Villa

Bar Harbor house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 9

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$738

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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Price per night from

$426

Brookhouse: A Cottage by the Sea

Prospect Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$197

Virginia's Sunset at Sunset Cottages

Bernard cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$153

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Price per night from

$299

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

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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$181

Pauls Cottage @ Seaside Cottages, Mt Desert Acadia

Southwest Harbor cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$394

Pristine oceanfront cottage

Milbridge cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$295

Test Property S2-Signup

Birch Harbor boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$1,033

Idyllic Suite, Ocean and Island Views near Acadia

Southwest Harbor apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$162

Perfect Downtown Bar Harbor Location Holland Ave Vacation Rentals

Bar Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$402

Downtown Bar Harbor Near Ocean - Holland Ave Vacation Rentals

Bar Harbor house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

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$299

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

Southwest Harbor cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$574

Cozy Home in Bar Harbor - Acadia in your Backyard

Bar Harbor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$224

Summertime -- Your Home in Bar Harbor

Bar Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$339

20ft. Lofted Ceilings Facing Acadia National Park

Hulls Cove house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$339

Hidden Gem in Bar Harbor - Acadia is your Backyard

Hulls Cove house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$239

SUMMERTIME COTTAGES BAR HARBOR

Hulls Cove house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$804

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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$186

Return to Beauty

Bar Harbor house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,091

Kinfolk Cottage

Southwest Harbor house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$402

Acorn Cottage

Bar Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$327

The Command Post: Oceanview overlooking Somes Sound

Mount Desert house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$131

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

Beautiful ocean view close to Seawall

Southwest Harbor apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 56 minutes

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Price per night from

$241

Bar Harbor Getaway

Bar Harbor house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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$230

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

Bernard cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$414

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

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

Mount Desert house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$420

Pond View - sweet little apt near Acadia National Park

Bar Harbor apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$118

Top o' the Ridge - beautiful views, private dock on Long Pond

Mount Desert cottage

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

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$495

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$360

“Absolute best house -” Wonderful home right on point in Bar Harbor - spend evenings watching the sunset on the rocks - only wish it had more bedrooms -

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$690

Norway House - modern post & beam in the heart of Mt Desert Island & Acadia

Bar Harbor cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$273

The Big House - waterfront privacy near Acadia National Park-Minimum 28 day

Bar Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

“Amazing...” This property was the best we could have asked for. We wanted a view and got it. We wanted to be secluded and got it. We could not have had a better time and recommend this house to anyone.

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Price per night from

$294

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