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

Winter Harbor Holiday Rentals

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Our top choices for Winter Harbor holiday rentals

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, (59 reviews)
"Relaxing secluded location "
United States
TOM G.
The price is NZ$1,691
includes taxes & fees
7 Sept - 8 Sept
Quaint and rustic cottage nestled on the shores of a small Maine village.

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, (7 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 NZ$518
includes taxes & fees
20 Aug - 21 Aug
Moonshine a cozy studio apartment with views of Bunker's Harbor

3. Hinckleys Dreamwood Cottages

Hinckleys Dreamwood Cottages
3.0 star property
Bar Harbor
7.8 out of 10, Good, (114 reviews)
"Perfect spot"
United States
Hanorah
The price is NZ$511
includes taxes & fees
7 Sept - 8 Sept
Hinckleys Dreamwood Cottages

4. Water access house Acadia National Park Schoodic Point

Water access house Acadia National Park Schoodic Point
Gouldsboro
9.4 out of 10, Exceptional, (47 reviews)
"Everything we needed for a quick family weekend getaway!"
United States
Paul T.
The price is NZ$951
includes taxes & fees
13 Aug - 14 Aug
Water access house Acadia National Park Schoodic Point

5. Hanscom's Motel and Cottages

Hanscom's Motel and Cottages
3.0 star property
Bar Harbor
9.4 out of 10, Exceptional, (368 reviews)
"Highly recommend this place!"
United States
Sarmila
The price is NZ$388
includes taxes & fees
31 Aug - 1 Sept
Hanscom's Motel and Cottages

6. 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, (4 reviews)
"Lovely communal campsites close to the action in Ellsworth and Acadia. Well-equipped space for cooking and dishes. Neighborhood is cute and quiet, and we enjoyed hearing the nearby roosters in the morning!"
United States
Emily M.
The price is NZ$123
includes taxes & fees
20 Aug - 21 Aug
Chickadee Hollow: Rustic Eco Camping near Acadia National Park!

7. Sun Shed Farm Stay

Sun Shed Farm Stay
Milbridge
8.6 out of 10, Excellent, (9 reviews)
"The sunshed is delightful -- the windows over the bed mean a lovely view for falling asleep and waking. The outdoor shower and compost toilet were clean and the shower pressure was great. Heads up if you'll be arriving after dark -- signage is small and the lighting is minimal to non-existent. Also would have been great to have a flashlight in the shed (be sure to bring yours/have your phone charged and ready)."
United States
Kelsey
The price is NZ$187
includes taxes & fees
20 Aug - 21 Aug
Sun Shed Farm Stay

8. 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 NZ$247
includes taxes & fees
19 Aug - 20 Aug
Miners Den Balsam Hill Cabins Milbridge

9. Cozy Milbridge Country Home

Cozy Milbridge Country Home
Milbridge
10.0 out of 10, Exceptional, (14 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 NZ$468
includes taxes & fees
21 Aug - 22 Aug
Cozy Milbridge Country Home

10. Little Brook Cottage Mount Desert Island “Pet Friendly”

Little Brook Cottage Mount Desert Island “Pet Friendly”
Tremont
9.6 out of 10, Exceptional, (167 reviews)
"We loved our stay at little brook cottage! Robbin was a fantastic host and very good with our dog! "
United States
Amir Ali P.
The price is NZ$598
includes taxes & fees
14 Aug - 15 Aug
Little Brook Cottage Mount Desert Island “Pet Friendly”

11. Stagecoach Stop

Stagecoach Stop
Milbridge
6.0 out of 10, (2 reviews)
"Great rustic lodging. Helpful and friendly host. Beautiful area and close to many hiking trails in parks and preserves. Highly recommended if you want simple, rustic lodging with comfortable accommodations (nice bed, everything needed for a compact kitchen to prepare meals, and nice picnic table for eating outdoors). "
United States
Eric L.
The price is NZ$272
includes taxes & fees
21 Aug - 22 Aug
Stagecoach Stop

12. Oceanfront Sunset View Cabin

Oceanfront Sunset View Cabin
Milbridge
9.8 out of 10, Exceptional, (6 reviews)
"The cabin and location were great. Enjoyed our time up there. "
United States
Art L.
The price is NZ$899
includes taxes & fees
11 Aug - 12 Aug
Oceanfront Sunset View Cabin

13. Downtown Apartments in Bar Harbor

Downtown Apartments in Bar Harbor
3.0 star property
Downtown Bar Harbor
9.4 out of 10, Exceptional, (11 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 NZ$925
includes taxes & fees
7 Sept - 8 Sept
Downtown Apartments in Bar Harbor

14. Isleview Gallery Rm 11 - Walk to lobster shacks!

Isleview Gallery Rm 11 - Walk to lobster shacks!
Trenton
9.6 out of 10, Exceptional, (5 reviews)
"Everything was so great about this spot and I would definitely comeback!"
United States
Nathan
The price is NZ$376
includes taxes & fees
1 Sept - 2 Sept
Isleview Gallery Rm 11 - Walk to lobster shacks!

15. Acadia Suites

Acadia Suites
3.0 star property
Bar Harbor
9.6 out of 10, Exceptional, (5 reviews)
"One picture in the description showed water so I thought the property was on water. Otherwise everything else was great and as described."
United States
Jennifer
The price is NZ$586
includes taxes & fees
1 Sept - 2 Sept
Acadia Suites

16. Day Trip to Acadia: Quiet Coastal Maine Escape

Day Trip to Acadia: Quiet Coastal Maine Escape
3.0 star property
Harrington
The price is NZ$641
includes taxes & fees
12 Aug - 13 Aug
Day Trip to Acadia: Quiet Coastal Maine Escape

17. Cozy Coastal Cabin #1

Cozy Coastal Cabin #1
Steuben
9.8 out of 10, Exceptional, (7 reviews)
"Cabin was exactly as listed and very clean. "
United States
AMANDA
Cozy Coastal Cabin #1

18. 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 NZ$421
includes taxes & fees
26 Aug - 27 Aug
20 Stunning Acadia Lodge w/AC Open Hearth Inn

19. Booking now for summer & fall 2026-explore Acadia, Bar Harbor, Downeast Maine

Booking now for summer & fall 2026-explore Acadia, Bar Harbor, Downeast Maine
Franklin
9.8 out of 10, Exceptional, (58 reviews)
"Such a cute house with lots of charm. Host was super responsive! We will definitely stay here again when we come back. "
United States
Staci D.
The price is NZ$1,019
includes taxes & fees
7 Sept - 8 Sept
Booking now for summer & fall 2026-explore Acadia, Bar Harbor, Downeast Maine

20. Oceanfront Cottage • Firepit + Beach • Near Acadia & Bar Harbor

Oceanfront Cottage • Firepit + Beach • Near Acadia & Bar Harbor
Milbridge
10.0 out of 10, Exceptional, (5 reviews)
"Nathan's place is a wonderful, quiet and quaint getaway location."
United States
Charles B.
The price is NZ$841
includes taxes & fees
10 Aug - 11 Aug
Oceanfront Cottage • Firepit + Beach • Near Acadia & Bar Harbor
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

Find out more about Winter Harbor

Everything you need to know about Winter Harbor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Harbor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winter Harbor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Harbor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Harbor holiday rentals we have selected for you start as low as NZ$123 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winter Harbor rentals

At Expedia, we put the best Winter Harbor holiday 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 holiday.

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 holiday rentals in Winter Harbor?

Yes, there are holiday rentals close to the most popular sights in Winter Harbor, or you can select a more secluded option if you're looking for a relaxing stay. Winter Harbor is known for its waterfront and musical theatre. Make sure you have time to check out the seafood restaurants and golf courses during your trip.

What are some of the best holiday rentals that Winter Harbor has to offer?

House near Acadia National Park: This holiday 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 that you can cook with friends or family.

How many holiday rentals are there in Winter Harbor?

Expedia has 19 holiday 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 holiday rental in Winter Harbor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winter Harbor. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family trips or small group gatherings.