Winter Harbor Rentals

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132 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!!!

Price per night from

$315

Schoodic Point Cottage

Winter Harbor cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$135

The Schoodic Apartment

Winter Harbor apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$111

Winter Harbor Apartment (aka: Fred's Place)

Winter Harbor apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$111

Great rentals within 20 miles that match your search

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.

Responds fast! avg. 41 minutes

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.

Price per night from

$229

Cottage with Mountain and Harbor Views on MDI

Southwest Harbor house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$372

Summer Cottage Nestled in the Woods

Southwest Harbor house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$206

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Birch Harbor boathouse

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$1,030

Oceanfront Schoodic Peninsula Log Home - 3 Bedrooms, 2.5 Baths Air-Conditioned

Gouldsboro house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$572

Shore Cottage with Ocean and Lighthouse Views

Steuben cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$148

Brookhouse: A Cottage by the Sea

Prospect Harbor cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$196

Virginia's Sunset at Sunset Cottages

Bernard cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$153

Price per night from

$298

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

Southwest Harbor cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 32 minutes

Price per night from

$474

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!

Price per night from

$286

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

Southwest Harbor apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 32 minutes

Price per night from

$245

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

Southwest Harbor apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 32 minutes

Price per night from

$180

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

Mount Desert cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 32 minutes

Price per night from

$278

Pauls Cottage @ Seaside Cottages, Mt Desert Acadia

Southwest Harbor cottage

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 32 minutes

Price per night from

$393

Shubert Bungalow

Seal Harbor cottage

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect!” The Shubert Bungalow was such a nice place to stay.It was so clean and there was everything that you neeeded in it.You could relax out on the deck or in the rocking chairs out front.One of the best things was that you could walk right to the carriage roads or walk to Jordan Park for lunch or dinner.It was the best place we ever stayed at.I would definitely go back!

Price per night from

$229

Pristine oceanfront cottage

Milbridge cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$294

Idyllic Suite, Ocean and Island Views near Acadia

Southwest Harbor apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$162

The Command Post: Oceanview overlooking Somes Sound

Mount Desert house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$131

Beautiful ocean view close to Seawall

Southwest Harbor apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 31 minutes

Price per night from

$241

Perfect Downtown Bar Harbor Location Holland Ave Vacation Rentals

Bar Harbor house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 52 minutes

Price per night from

$401

Downtown Bar Harbor Near Ocean - Holland Ave Vacation Rentals

Bar Harbor house

4 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 52 minutes

Price per night from

$298

Haiku House - your gateway to Acadia

Acadia National Park cottage

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$544

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

Bar Harbor house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 3 hours 52 minutes

Price per night from

$401

Deer Track, Cabin Overlooking Somes Sound

Mount Desert house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$148

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

Southwest Harbor cottage

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$572

Long pond, amazing sunsets, quiet

Mount Desert house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$744

Settlers House - Lodging on the park loop

Birch Harbor house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$180

Captain's Quarters at Captain Bennis House

Sullivan apartment

2 bedrooms / 2 bathrooms / sleeps 3

Responds fast! avg. 48 minutes

Price per night from

$115

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.

Price per night from

$186

Price per night from

$344

Waterfront JCR Taunton Bay Hideaway w/ Kayaks!!!

Sullivan house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 48 minutes

Price per night from

$328

Lucky Stone Retreat - private beach & Acadia view

Sullivan house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$428

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