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Winter Harbor Rentals

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112 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!!!

Responds fast! avg. 16 minutes

Price per night from

$303

Schoodic Point Cottage

Winter Harbor cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 20 minutes

Price per night from

$113

The Schoodic Apartment

Winter Harbor apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 20 minutes

Price per night from

$92

Winter Harbor Apartment (aka: Fred's Place)

Winter Harbor apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 20 minutes

Price per night from

$92

Captain Guptill House steps from the waters edge in Winter Harbor

Winter Harbor house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$277

Guptill Cottage on Schoodic Point, Winter Harbor

Winter Harbor house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$244

The Boat House on Guptill Point

Winter Harbor cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$244

Great rentals within 20 miles that match your search

Little Island House Upstairs Appartment

Bass Harbor house

1 bedroom / 1 bathroom / sleeps 2

“Perfect slice of Peace” The Little Island House is the perfect place to stay when you journey to Maine. It is located in Bass Harbor, which is a peaceful village where lobster fishermen and women come and go. Less than a block from the house is a place to purchase crab and live lobster which you can steam in a kitchen which has Everything you could possibly need. If you are not interested in cooking, a wharf restaurant is close by and will meet your every need. The bed and bedding were perfect. Everything was very comfortable. From your little house, you can quickly jump to other villages and acadia National Park. My favorite part was sitting on the porch watching boats come in and out of the harbor. We also took a boat trip which left from the dock near the house. We saw the part of Maine that you can only see from a boat.

Price per night from

$192

Sea Ledge at Sandcliff by the Sea

Bar Harbor house

3 bedrooms / 2 bathrooms / sleeps 6

“Comfortable Stay with Amazing Bedroom Ocean View” My husband and I stayed at Sandcliff by the Sea for our 1 year wedding anniversary. What a comfortable, beautiful home with an outstanding view of Frenchman's Bay from the Bedroom Deck! We ate breakfast every morning watching the boats sail by while smelling the salt air. We were looking for complete relaxation…and Sandcliff by the Sea delivered this. Every night during our stay I enjoyed the master bedroom jacuzzi..it's down right amazing! Now if I can only convince my husband that we need one at home :) You can also hike from the back yard and enjoy wild blueberries along the way! Lastly we were very impressed with how clean the house was upon our arrival. Thank you very much Bonnie! We will definitely be back again in the future. Jen :)

Price per night from

$456

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.

Price per night from

$407

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

$228

Family Friendly Farmhouse with fantastic views

Southwest Harbor house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$440

Cottage with Mountain and Harbor Views on MDI

Southwest Harbor house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$371

Summer Cottage Nestled in the Woods

Southwest Harbor house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$205

Hot Tub+AIR CONDITIONING+Fire Pit+Views & Access to Somes Sound

Mount Desert cottage

2 bedrooms / 1 bathroom / sleeps 7

“Absolutely fantastic!” We had a fantastic stay at The acadia. We were probably some of the first tourists of the season (mid april) and it was pretty chilly, so the hot tub was a very welcome amenity. The owners were wonderful, taking the time to show us around upon arrival and even brought over a new grill right away when we realized the original wasn't working. The cottage was just the right size for four people--cozy but comfortable. Everything was very clean and the views were beautiful. We cooked our own lobster and ate out on the deck on night. Another night we had a fire in the fire pit and drank wine and roasted marsh-mellows. I would absolutely stay here again and recommend it to anyone heading to acadia.

Price per night from

$293

Victorian Home-Northeast Harbor, Maine-Acadia Park

Northeast Harbor house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$309

Shore Cottage with Ocean and Lighthouse Views

Steuben cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$147

Brookhouse: A Cottage by the Sea

Prospect Harbor cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$195

Price per night from

$297

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

Southwest Harbor cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 13 minutes

Price per night from

$261

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!

Responds fast! avg. 2 hours 38 minutes

Price per night from

$285

Lito Lodge - Oceanfront near Acadia

Lamoine house

3 bedrooms / 3 bathrooms / sleeps 7

“Perfect get-away home.” You can't beat a quiet morning cup of coffee on the deck overlooking the bay and watching the lobstermen hauling in their traps. The beautiful starry night skies are also an amazing sight. This spacious lodge had more amenities than we dreamed of. Peaceful and secluded with a gorgeous view but close to many antique shops, Acadia N.P., Bar Harbor, places to buy lobsters, and other attractions. Something for everyone! We often saw Bald Eagles on our way down the long driveway. On the morning that we had to leave, I stood on the deck gazing across the water, and was joined 1 by 1 by each member of our family, each of us having the same thought- we did not want to leave! We would highly recommend this rental and hope to return some day!

Price per night from

$342

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. 2 hours 13 minutes

Price per night from

$179

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. 2 hours 13 minutes

Price per night from

$179

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

Mount Desert cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 13 minutes

Price per night from

$261

Pauls Cottage @ Seaside Cottages, Mt Desert Acadia

Southwest Harbor cottage

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 13 minutes

Price per night from

$342

Fabulous Bar Harbor Log Home, Minutes from Acadia

Bar Harbor house

3 bedrooms / 2 bathrooms / sleeps 8

“Heaven on Earth !” We have traveled and stayed in the Chalet many times. It is our # 1 place to be. We go in the winter time and have made many memories there. Brenda Harp always aims to please and is very accommodating. The Chalet sits by itself in an amazing woods with amazing views of the Bay. We have seen seal, eagles, and deer to name a few. The sunsets there are the best I've seen in my life. We have made many many special and life long memories there and would Highly recommend it. 10 or more stars. Jon and Charleen

Price per night from

$349

Pristine oceanfront cottage

Milbridge cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$269

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Birch Harbor boathouse

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$1,026

Beautiful ocean view close to Seawall

Southwest Harbor apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 41 minutes

Price per night from

$240

Idyllic Suite, Ocean and Island Views near Acadia

Southwest Harbor apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$161

Acadia National Park and Quiet Fields

Seal Cove apartment

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$143

The Command Post: Oceanview overlooking Somes Sound

Mount Desert house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$130

Haiku House - your gateway to Acadia

Acadia National Park cottage

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$542

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

Southwest Harbor cottage

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$570

Deer Track, Cabin Overlooking Somes Sound

Mount Desert house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$147

Quintessential Rustic Maine Oceanfront Cottage with Sunset Views

Tremont cottage

2 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 1 hour 10 minutes

Price per night from

$318

Acadiacamper rentals delivered to campground

Southwest Harbor caravan/mobile home

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$114

Viewing 38 of 112
rentals in Winter Harbor

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Top Destination reviews

ACADIA National Park. Walk to Ocean, Restaurants! Private Deck Mountain VIEW
Great family stay

We have 4 generations staying here for several nights. First of all the owners were wonderful to work with and the home had everything we needed to have a wonderful time. There was plenty of space for everyone and we enjoyed walking into Winter Harbor to explore, get groceries and to eat. It was a great place to relax after taking the ferry across to Bar Harbor and we could get away from all the hustle and bustle. We would definitely stay here again.see more
Captain Guptill House steps from the waters edge in Winter Harbor
Girls trip

To start off the house was just as beautiful, if not more so, than the pictures. If you are looking for a nice place to relax, take some time off from your crazy lives, this is definitely the place to do it. The town is small and quaint and the people were friendly and so helpful with directions and suggestions.We were fortunate enough to meet the owners of the home and they were just wonderful people, so welcoming and you could tell they loved being part of the community in Winter Harbor. There is part of the Acadia Forest a mile or two from the main part of town where you can hike and bike and see beautiful things. There is a convenient island ferry that can take you back and forth to Bar Harbor for some additional shopping, tours, and restaurants. I will be back again someday to this beautful home and area.see more

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