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Winter Harbor Vacation Rentals

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Vacation Rentals in Winter Harbor

One-of-kind estate with unique & luxurious decor and wooded oceanside location.

10.0 out of 10, Exceptional, (23)
"Great house and great area to visit."
One-of-kind estate with unique & luxurious decor and wooded oceanside location.

Charming Coastal House with Cozy Living Spaces and Outdoor Firepit

8.0 out of 10, Very Good, (3)
"We loved the location in Winter Harbor. Close to lots of great places and it was nice and quiet. Would definitely stay here again!"
Charming Coastal House with Cozy Living Spaces and Outdoor Firepit

Stone Park

4.0 star property
9.0 out of 10, Wonderful, (113)
"Super clean and nice place for family staying"
The price is ¥38,284
¥41,729 total
includes taxes & fees
Aug 18 - Aug 19
Stone Park

Hinckleys Dreamwood Cottages

3.0 star property
7.2 out of 10, Good, (67)
"Quiet cottage in the middle of everything we love to do in Bar Harbor."
The price is ¥35,767
¥46,346 total
includes taxes & fees
Aug 24 - Aug 25
Hinckleys Dreamwood Cottages

Hanscom's Motel and Cottages

3.0 star property
9.4 out of 10, Exceptional, (279)
"Wonderful stay"
The price is ¥30,044
¥32,748 total
includes taxes & fees
Sep 4 - Sep 5
Hanscom's Motel and Cottages

Bring everything to camp minus the tent at our little cabin.

10.0 out of 10, Exceptional, (112)
"We loved the location and seclusion of the cabin and it was so close to everything we wanted to visit in Maine."
Bring everything to camp minus the tent at our little cabin.

Downtown Apartments in Bar Harbor

3.0 star property
9.2 out of 10, Wonderful, (9)
"Cute and tidy apartment, close to downtown but not too close and we were very happy with our stay. "
The price is ¥52,105
¥78,874 total
includes taxes & fees
Aug 18 - Aug 19
Downtown Apartments in Bar Harbor

210 Main St

3.0 star property
9.0 out of 10, Wonderful, (4)
"This apartment was so beautiful and located next to a charming Main Street with plenty of coffee shops, restaurants, bars, and cute shops. It was perfect for the 3 of us at the end of our trip. It’s pretty close to Acadia National Park without all the regular drama of the crowd in Bar Harbor."
The price is ¥22,488
¥42,911 total
includes taxes & fees
Aug 21 - Aug 22
210 Main St

Bar Harbor Condos

2.5 star property
10.0 out of 10, Exceptional, (4)
"Condo was so clean and full of great amenities. Good for small families. Walkable to main stuff in Bar Harbor and easy drive to Acadia. Owners great with communication. Would easily stay here again!"
The price is ¥57,261
¥62,414 total
includes taxes & fees
Aug 20 - Aug 21
Bar Harbor Condos

Charming Seaside Cottage with a Gas Fireplace, Spacious Patio, and Nearby Hiking

8.0 out of 10, Very Good, (1)
"The quietness of the area and close distance to Bar Harbor."
Charming Seaside Cottage with a Gas Fireplace, Spacious Patio, and Nearby Hiking

Lighthouse Cabins Maine

3.0 star property
10.0 out of 10, Exceptional, (113)
"Great little cabin, clean, comfortable and charming."
Lighthouse Cabins Maine

Lone Pine Oceanfront Cottage

10.0 out of 10, Exceptional, (36)
"We loved our stay at Lone Pine. The house was perfect for our family and we all enjoyed sitting outside and watching the tide go in and out. It was the perfect location for day trips to Acadia and Campobello island. "
Lone Pine Oceanfront Cottage

Narrows Too Camping Resort

2.0 star property
8.0 out of 10, Very Good, (31)
"Our cabin was ideal for two people. Very clean and had everything we needed."
The price is ¥31,499
¥34,334 total
includes taxes & fees
Aug 24 - Aug 25
Narrows Too Camping Resort

Private Indoor Pool Near Acadia National Park 25 mins from Bar Harbor

9.2 out of 10, Wonderful, (35)
"Beautiful area and the house was perfect for our group "
The price is ¥84,487
¥141,826 total
includes taxes & fees
Sep 16 - Sep 17
Private Indoor Pool Near Acadia National Park 25 mins from Bar Harbor

Family-Friendly Yurts with Onsite Games, Hiking & Wellness Amenities

10.0 out of 10, Exceptional, (29)
"The yurt glamping was perfect. The property is amazing with activities and we were able to collect a couple eggs from the hens. Highly recommend this stay for any occasion. "
The price is ¥60,201
¥91,129 total
includes taxes & fees
Sep 2 - Sep 3
Family-Friendly Yurts with Onsite Games, Hiking & Wellness Amenities

Cottage with a Vista

9.6 out of 10, Exceptional, (94)
"Property owner was on site and very helpful/knowledgeable about the area and friendly. Property is beautiful and well kept. Area was very quiet and peaceful. Would highly recommend for a getaway. "
The price is ¥24,581
¥44,441 total
includes taxes & fees
Sep 4 - Sep 5
Cottage with a Vista

Anny's Treetop on the Quietside Mt Desert Island,& Acadia National Park

9.6 out of 10, Exceptional, (10)
"Anny’s is homey, comfortable and fully equipped vacation rental. "
The price is ¥42,685
¥60,485 total
includes taxes & fees
Aug 18 - Aug 19
Anny's Treetop on the Quietside Mt Desert Island,& Acadia National Park

Spectacular Ocean Views, Walking Distance To Town, Bike Into Acadia

9.8 out of 10, Exceptional, (81)
"Great property for 3 generation family vacation. Plenty of room to spread out. Well supplied with necessities. Gorgeous outdoor space. Perfect location walkable to everything. Would definitely book again if vacationing in the area. "
Spectacular Ocean Views, Walking Distance To Town, Bike Into Acadia

Oceanfront Sunset View Cabin

10.0 out of 10, Exceptional, (1)
"Quiet and Secluded. We had a great time sitting around the fire, great memories, very clean, The kids had a great time. The top bunk mattress was fine for my 8 year old but would have been a bit stiff for me. My older son slept on the futon he loved it. Plenty of towels, The water heater is a small one but we could each get nice hot showers if we waited a bit between. It would reheat quickly for the next shower. "
The price is ¥36,650
¥63,533 total
includes taxes & fees
Sep 2 - Sep 3
Oceanfront Sunset View Cabin

Seawall Retreat! Close to Ocean & Acadia!

9.0 out of 10, Wonderful, (9)
"This cabin is perfect for a small family with a car. It’s in the middle of everything. It’s a basic house but has everything you need- nice hot shower, cooking utensils, camp fire, etc. I still dream of the naps we had on the sofa. The surroundings are peaceful with lots of deer strolling by. "
Seawall Retreat! Close to Ocean & Acadia!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Harbor Hotel Reviews

Frequently asked questions

Are there vacation rentals in Winter Harbor?

Yes, we have vacation rentals close to well known attractions in Winter Harbor, or you can go with a more remote option if you're looking for a relaxing stay. Winter Harbor is known for its waterfront and musical theater. Make sure you have time to check out the seafood restaurants and golf courses during your trip.

What's the top vacation rental that Winter Harbor has to offer?

House near Acadia National Park: This vacation home rental outside of Winter Harbor is located in a national park and offers a fireplace, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and an oven, so you can cook with friends or family.

How many vacation rentals are there in Winter Harbor?

Expedia has 17 vacation rentals for your stay in Winter Harbor.

What’s there to see and do in Winter Harbor?

Acadia National Park and Schoodic Peninsula are a couple of lovely local spots to get outside and enjoy nature. Schoodic Point and Grindstone Neck Golf Course are other places to visit while you're in town.

What’s a vacation rental in Winter Harbor like?

Vacation rentals are private properties where you can stay for short or long periods in Winter Harbor. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip.