Photo by Ricky Batista

Winter Harbor Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Winter Harbor

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

10.0 out of 10, Exceptional, (25)
"Great house and great area to visit."
The price is NZ$6,615
includes taxes & fees
23 Oct - 24 Oct
One-of-kind estate with unique & luxurious decor and wooded oceanside location.

Stone Park

4.0 star property
9.0 out of 10, Wonderful, (136)
"It was very beautiful, clean, and everyone was very nice. "
The price is NZ$300
includes taxes & fees
19 Oct - 20 Oct
Stone Park

Hinckleys Dreamwood Cottages

3.0 star property
7.4 out of 10, Good, (81)
"Close to Acadia and Bar Harbor. The cabins are older but they are clean. The staff was polite and helpful. I would stay there again. "
The price is NZ$503
includes taxes & fees
25 Sept - 26 Sept
Hinckleys Dreamwood Cottages

Hanscom's Motel and Cottages

3.0 star property
9.4 out of 10, Exceptional, (300)
"Easy access to Acadia National Park and Bar Harbor."
The price is NZ$288
includes taxes & fees
19 Oct - 20 Oct
Hanscom's Motel and Cottages

Woodland Apartments-Acadia National Park

3.0 star property
8.0 out of 10, Very good, (5)
"Everything exceeded our expextations. The place was spotless. The road to get the rental was rough. You have to watch out for the pot holes but definitely not a deal breaker. "
The price is NZ$662
includes taxes & fees
29 Sept - 30 Sept
Woodland Apartments-Acadia National Park

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

10.0 out of 10, Exceptional, (115)
"I liked that it was pet friendly, and had paddle boards for use! It was a beautiful cabin, and suited our needs and wants perfectly! We plan on coming back next year!"
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, (10)
"The location was great to walk to almost everything. Was able to take a trolley to the park for a tour which we would highly recommend. The room was very clean. Shower was great lots of pressure. The gifts that were left in the place was very thoughtful. Would definitely recommend for anyone we know coming to Maine - bar harbor. "
The price is NZ$954
includes taxes & fees
28 Sept - 29 Sept
Downtown Apartments in Bar Harbor

210 Main St

3.0 star property
9.2 out of 10, Wonderful, (5)
"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 NZ$460
includes taxes & fees
23 Oct - 24 Oct
210 Main St

House near Acadia National Park

4.0 star property
10.0 out of 10, Exceptional, (21)
"Great place, close to the main road."
The price is NZ$923
includes taxes & fees
19 Oct - 20 Oct
House near Acadia National Park

Bar Harbor Main Street Apartments

3.5 star property
9.2 out of 10, Wonderful, (7)
"Great location, incredible breakfast. Air conditioner is extremely loud though!"
The price is NZ$952
includes taxes & fees
19 Oct - 20 Oct
Bar Harbor Main Street Apartments

Beautiful Apartments in Thorsen Road Maine

3.0 star property
8.4 out of 10, Very good, (9)
"Very nice, clean, new, good towels, great new on the outskirts of Hancock. I extended my stay a couple of extra days and they were very accommodating. I will stay here again. "
The price is NZ$563
includes taxes & fees
28 Sept - 29 Sept
Beautiful Apartments in Thorsen Road Maine

Genuine Farm experience! Barn loft on Organic Farm—pet pig and chickens below!

10.0 out of 10, Exceptional, (1)
"This quaint stay was everything we needed for our trip to MDI. Becka was a wonderful host (as was her angelic dog, Cayenne), and we loved the rustic setting. The rental was well and thoughtfully stocked. The outdoor shower was so enjoyable, serenaded by the nearby apiary. Even the early bird rooster made us laugh. Would happily stay again."
Genuine Farm experience! Barn loft on Organic Farm—pet pig and chickens below!

Private And Cozy Tiny Home For Your Acadia Escape. Pet Friendly with Kayaks.

10.0 out of 10, Exceptional, (21)
"We had a great time staying here - super cute and cozy. We were able to cook in most nights and the pond for kayaking was so beautiful. Really enjoyed staying on the quieter side of Acadia and the drive to the main Acadia area was easy and scenic! "
The price is NZ$731
includes taxes & fees
19 Oct - 20 Oct
Private And Cozy Tiny Home For Your Acadia Escape. Pet Friendly with Kayaks.

Perfectly Centered in Birch Harbor Village! Unit 4

10.0 out of 10, Exceptional, (39)
"The stay was perfect. Very clean and I will stay there again"
Perfectly Centered in Birch Harbor Village! Unit 4

Bar Harbor Condos

2.5 star property
10.0 out of 10, Exceptional, (6)
"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 NZ$645
includes taxes & fees
28 Sept - 29 Sept
Bar Harbor Condos

Historic 1940s lakeside cabin on spring-fed pond. Close to Acadia National Park

10.0 out of 10, Exceptional, (15)
"The cabin and property were as listed. Communication with the property manager was great! Thoughtful, friendly and easy to work with. Beautiful lake, rustic and fun. We really enjoyed our stay. The cabin was older but very well kept. Nice and close to Bar Harbor and Acadia Park (about 40 minutes)."
Historic 1940s lakeside cabin on spring-fed pond. Close to Acadia National Park

Quiet and Cozy Seaside Cottage with Amazing Sunsets

9.8 out of 10, Exceptional, (57)
"Wonderful place to relax with lots of ammenities!"
Quiet and Cozy Seaside Cottage with Amazing Sunsets

Lighthouse Cabins Maine

3.0 star property
10.0 out of 10, Exceptional, (122)
"Great spot to stay in Maine"
Lighthouse Cabins Maine

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

9.4 out of 10, Exceptional, (3)
"Very charming place with a lot of attention to detail which made it feel like home."
Charming Seaside Cottage with a Gas Fireplace, Spacious Patio, and Nearby Hiking

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

9.8 out of 10, Exceptional, (82)
"Landmark 1910 Shingle-style mansion centrally located next to downtown Bar Harbor, just steps from the sand bar to Bar Island. House was as advertised; maintenance and operating features fine; booking and check-in process smooth. A perfect venue for an extended family reunion. (We booked the house for my wife's 70th birthday.)"
Spectacular Ocean Views, Walking Distance To Town, Bike Into 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Harbor Hotel Reviews

Find out more about Winter Harbor

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$288 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. 

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 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 that you can cook with friends or family. Another good choice for your trip to Winter Harbor is One-of-kind estate with unique & luxurious decor and wooded oceanside location..

How many holiday rentals are there in Winter Harbor?

Expedia has 17 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.