A coastal town with a lighthouse, rocky shoreline, dense forest, and a clear blue sky.

Winter Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winter Harbor vacation rentals

Property grounds

1. Quaint and rustic cottage nestled on the shores of a small Maine village.

Quaint and rustic cottage nestled on the shores of a small Maine village.
Winter Harbor
10.0 out of 10, Exceptional, (65 reviews)
"Exceptional property, great views and quiet. Just perfect for us."
United States
Umesh K.
The price is ￥53,662
￥148,067 total
includes taxes & fees
Sep 24 - Sep 25
Quaint and rustic cottage nestled on the shores of a small Maine village.
Room

2. Moonshine a cozy studio apartment with views of Bunker's Harbor

Moonshine a cozy studio apartment with views of Bunker's Harbor
Gouldsboro
10.0 out of 10, Exceptional, (10 reviews)
"We loved the view of the harbor, the quietness of the area, and the adjacent restaurant (great coffee). The owner was very kind and our stay was lovely. "
United States
Lori
The price is ￥30,664
￥47,796 total
includes taxes & fees
Sep 24 - Sep 25
Moonshine a cozy studio apartment with views of Bunker's Harbor
Property grounds

3. Brand New House!! Charming tiny home close to Schoodic Peninsula.

Brand New House!! Charming tiny home close to Schoodic Peninsula.
Gouldsboro
The price is ￥34,497
￥61,667 total
includes taxes & fees
Sep 14 - Sep 15
Brand New House!! Charming tiny home close to Schoodic Peninsula.
Property grounds

4. Cozy lodge minutes from Acadia National Park's Schoodic Loop!

Cozy lodge minutes from Acadia National Park's Schoodic Loop!
Gouldsboro
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥34,738
￥53,010 total
includes taxes & fees
Sep 16 - Sep 17
Cozy lodge minutes from Acadia National Park's Schoodic Loop!
Courtyard

5. Hanscom's Motel and Cottages

Hanscom's Motel and Cottages
3.0 star property
Bar Harbor
9.4 out of 10, Exceptional, (386 reviews)
"Very responsive cute place to stay at near bar harbor"
United States
Hannah
The price is ￥28,363
￥30,915 total
includes taxes & fees
Sep 20 - Sep 21
Hanscom's Motel and Cottages
Luxury Cabin, Hot Tub (Pets Not Allowed) | Exterior

6. Hinckleys Dreamwood Cottages

Hinckleys Dreamwood Cottages
3.0 star property
Bar Harbor
7.8 out of 10, Good, (126 reviews)
"We had a good experience there. Campfires , swimming pool, and camping tables are publicly shared, but inside the cottage everything is perfect."
United States
Muyuan
The price is ￥30,931
￥49,046 total
includes taxes & fees
Sep 13 - Sep 14
Hinckleys Dreamwood Cottages
City Apartment, 1 King Bed with Sofa bed, Kitchen | Living area

7. Downtown Apartments in Bar Harbor

Downtown Apartments in Bar Harbor
3.0 star property
Downtown Bar Harbor
9.2 out of 10, Wonderful, (15 reviews)
"The location was great! It's close to a lot of restaurants and gift shops. The unit was on the second floor, so it was a little bit challenging for me because I have bad knees, but we're very satisfied with the place. It's not too far from Acadia National Park. I would recommended it. The communication with host was fast."
United States
Thuynga
The price is ￥37,470
￥67,860 total
includes taxes & fees
Sep 13 - Sep 14
Downtown Apartments in Bar Harbor
Exterior

8. Water access house Acadia National Park Schoodic Point

Water access house Acadia National Park Schoodic Point
Gouldsboro
9.2 out of 10, Wonderful, (50 reviews)
"The house was comfortable and clean. We enjoyed the fire pit and charcoal grill. Jeff was very friendly and helpful. The location was wonderful for exploring Acadia and especially the Schoodic Peninsula."
United States
Linette
The price is ￥46,163
￥89,360 total
includes taxes & fees
Oct 1 - Oct 2
Water access house Acadia National Park Schoodic Point
Property grounds

9. Isleview Gallery Rm 12 - 10 min to Acadia!

Isleview Gallery Rm 12 - 10 min to Acadia!
Trenton
9.4 out of 10, Exceptional, (13 reviews)
"This property is close to Acadia it was a very easy drive. The hosts were very helpful and kept a free stocked kitchen in the office area, this touch made it feel like you were staying with family or friends. I stayed in room 12 it is very small. Perfect for solo travelers."
United States
Luann W.
The price is ￥21,301
￥31,969 total
includes taxes & fees
Sep 13 - Sep 14
Isleview Gallery Rm 12 - 10 min to Acadia!
Interior

10. Private 14 acre waterfront 3-bedroom cabin in the peaceful forests of Maine

Private 14 acre waterfront 3-bedroom cabin in the peaceful forests of Maine
Gouldsboro
10.0 out of 10, Exceptional, (6 reviews)
The price is ￥34,738
￥62,097 total
includes taxes & fees
Sep 13 - Sep 14
Private 14 acre waterfront 3-bedroom cabin in the peaceful forests of Maine
Room

11. Bar Harbor Condos

Bar Harbor Condos
2.5 star property
Bar Harbor
10.0 out of 10, Exceptional, (20 reviews)
"Clean, new and quiet. Excellent location. Absolutely perfect."
United States
Joy
The price is ￥37,644
￥41,032 total
includes taxes & fees
Sep 13 - Sep 14
Bar Harbor Condos
Living area

12. Downeast Maine Cottage with Water View

Downeast Maine Cottage with Water View
Steuben
10.0 out of 10, Exceptional, (20 reviews)
"Great cabin for a family get away to relax in nature. The cabin is spacious and very scenic."
United States
Amanda R.
The price is ￥34,429
￥84,143 total
includes taxes & fees
Sep 17 - Sep 18
Downeast Maine Cottage with Water View
Room

13. Sun Shed Farm Stay

Sun Shed Farm Stay
Milbridge
8.6 out of 10, Excellent, (12 reviews)
"Fun way to get off the beaten track, enjoyed waking up to some farm animals nearby, and the stars were incredible."
United States
Matthew
The price is ￥12,419
￥16,879 total
includes taxes & fees
Sep 13 - Sep 14
Sun Shed Farm Stay
Exterior detail

14. The Colonels Suites

The Colonels Suites
2.0 star property
Northeast Harbor
The price is ￥46,411
￥59,003 total
includes taxes & fees
Sep 18 - Sep 19
The Colonels Suites
Room

15. Camping at the Ice-Shack

Camping at the Ice-Shack
Milbridge
8.0 out of 10, Very Good, (2 reviews)
"It’s name says it all. A perfectly sized, literal “bed room” in the middle of the woods. The fire pit had wood all ready for me to use. If you were to come in the winter, the tiny home has a wood stove to use as well."
United States
Wesley H.
The price is ￥9,659
￥13,871 total
includes taxes & fees
Sep 13 - Sep 14
Camping at the Ice-Shack
Outdoor dining

16. Chickadee Hollow: Rustic Eco Camping near Acadia National Park!

Chickadee Hollow: Rustic Eco Camping near Acadia National Park!
Surry
10.0 out of 10, Exceptional, (7 reviews)
"The campsite was absolutely amazing. The different areas to camp in were great. There was plenty of space for a hammock, if we had brought one. The only complaint we had were the black flies, but those just come with the experience of being in nature!"
United States
Katherine B.
The price is ￥4,856
￥11,183 total
includes taxes & fees
Sep 12 - Sep 13
Chickadee Hollow: Rustic Eco Camping near Acadia National Park!
Terrace/patio

17. Cozy Milbridge Country Home

Cozy Milbridge Country Home
Milbridge
10.0 out of 10, Exceptional, (15 reviews)
"This was the best place we stayed by far!Exceptional amount of room, very helpful host, nice and quiet. It was like a home away from home."
United States
Gene B.
The price is ￥26,831
￥42,950 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Milbridge Country Home
Room

18. Lighthouse Cabins Maine

Lighthouse Cabins Maine
3.0 star property
Bass Harbor
10.0 out of 10, Exceptional, (148 reviews)
"Great place, nice hosts, good location away from the crazy of Bar Harbor."
United States
Michael
Lighthouse Cabins Maine
Terrace/patio

19. 20 Stunning Acadia Lodge w/AC Open Hearth Inn

20 Stunning Acadia Lodge w/AC Open Hearth Inn
Trenton
9.0 out of 10, Wonderful, (16 reviews)
"The hosts are very responsive. I do think better coffee would help -especially since the owners are Hawaiian! "
United States
Bernice G.
The price is ￥23,344
￥36,889 total
includes taxes & fees
Sep 17 - Sep 18
20 Stunning Acadia Lodge w/AC Open Hearth Inn
Property grounds

20. Miners Den Balsam Hill Cabins Milbridge

Miners Den Balsam Hill Cabins Milbridge
Milbridge
9.0 out of 10, Wonderful, (4 reviews)
"Such a beautiful place to stay! Super clean, super quiet, and easy to get to. Sienna was super communicative and kind. It’s hard not to fall in love with this cabin and want to stay forever, couldn’t recommend more!"
United States
Samantha D.
The price is ￥15,869
￥22,312 total
includes taxes & fees
Sep 13 - Sep 14
Miners Den Balsam Hill Cabins Milbridge
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

Comfort Inn Ellsworth - Bar Harbor

Comfort Inn Ellsworth - Bar Harbor

8/10 Good
"Extremely good staff. Breakfast was served well and room was clean. The hotel is located in a beautiful serene place. Overall we enjoyed the stay."
Lohitanvita 3-night trip
Posted less than an hour ago
Comfort Inn Ellsworth - Bar Harbor

Find out more about Winter Harbor

Search for holiday rentals in Winter Harbor on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Harbor using one of the methods below:

  • View our selection of featured holiday rentals in Winter Harbor
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Look no further and take a look at our great range of rental properties in Winter Harbor!

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 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 16 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.