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, (66 reviews)
"Exceptional property, great views and quiet. Just perfect for us."
United States
Umesh K.
$886 nightly
The price is $966
Sep 14 - Sep 15
Total with taxes and fees
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, (11 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
$284 nightly
The price is $310
Sep 18 - Sep 19
Total with taxes and fees
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
$372 nightly
The price is $405
Sep 15 - Sep 16
Total with taxes and fees
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)
$315 nightly
The price is $343
Sep 16 - Sep 17
Total with taxes and fees
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, (390 reviews)
"Very responsive cute place to stay at near bar harbor"
United States
Hannah
$204 nightly
The price is $222
Sep 20 - Sep 21
Total with taxes and fees
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
$302 nightly
The price is $320
Sep 16 - Sep 17
Total with taxes and fees
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)
"Cute and tidy apartment, close to downtown but not too close and we were very happy with our stay. "
United States
Rebecca
$508 nightly
The price is $538
Sep 20 - Sep 21
Total with taxes and fees
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
$531 nightly
The price is $579
Oct 1 - Oct 2
Total with taxes and fees
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.
$184 nightly
The price is $201
Sep 16 - Sep 17
Total with taxes and fees
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)
$369 nightly
The price is $402
Sep 14 - Sep 15
Total with taxes and fees
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
$434 nightly
The price is $473
Sep 30 - Oct 1
Total with taxes and fees
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.
$494 nightly
The price is $538
Sep 17 - Sep 18
Total with taxes and fees
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
$88 nightly
The price is $96
Sep 14 - Sep 15
Total with taxes and fees
Sun Shed Farm Stay
Exterior detail

14. The Colonels Suites

The Colonels Suites
2.0 star property
Northeast Harbor
$346 nightly
The price is $377
Sep 18 - Sep 19
Total with taxes and fees
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.
$69 nightly
The price is $75
Sep 14 - Sep 15
Total with taxes and fees
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.
$66 nightly
The price is $72
Sep 14 - Sep 15
Total with taxes and fees
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.
$244 nightly
The price is $266
Sep 14 - Sep 15
Total with taxes and fees
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.
$296 nightly
The price is $323
Oct 14 - Oct 15
Total with taxes and fees
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.
$124 nightly
The price is $135
Sep 14 - Sep 15
Total with taxes and fees
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

Colonial Inn Ellsworth

Colonial Inn Ellsworth

10/10 Excellent
"Excellent Facility staffs and cleans"
Andy 1-night trip
Posted less than an hour ago
Colonial Inn Ellsworth

Find out more about Winter Harbor

Everything you need to know about Winter Harbor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Harbor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Harbor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Harbor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Harbor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Harbor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Harbor rentals

At Expedia, we put the best Winter Harbor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Harbor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.