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Winter Harbor Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

Holiday Rentals in Winter Harbor

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

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

10.0 out of 10, Exceptional, (25)
"The views are great and the host is pretty responsive too. Had an awesome time!"
The price is AU$5,407
includes taxes & fees
8 Oct - 9 Oct
One-of-kind estate with unique & luxurious decor and wooded oceanside location.
Stone Park
Building design

Stone Park

4.0 star property
9.2 out of 10, Wonderful, (153)
"Great stay"
Stone Park
Hinckleys Dreamwood Cottages
One Bedroom Cabin with Living Room, Kitchen & Wrap around Deck | Private kitchen

Hinckleys Dreamwood Cottages

3.0 star property
7.6 out of 10, Good, (84)
"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 AU$488
includes taxes & fees
19 Oct - 20 Oct
Hinckleys Dreamwood Cottages
Hanscom's Motel and Cottages
Courtyard

Hanscom's Motel and Cottages

3.0 star property
9.4 out of 10, Exceptional, (301)
"Easy access to Acadia National Park and Bar Harbor."
The price is AU$249
includes taxes & fees
3 Nov - 4 Nov
Hanscom's Motel and Cottages
Bring everything to camp minus the tent at our little cabin.
Miscellaneous

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

10.0 out of 10, Exceptional, (116)
"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.
Woodland Apartments-Acadia National Park
Exterior

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 AU$566
includes taxes & fees
20 Oct - 21 Oct
Woodland Apartments-Acadia National Park
210 Main St
Luxury Apartment, Non Smoking | Private kitchen

210 Main St

3.0 star property
9.4 out of 10, Exceptional, (6)
"Restaurants nearby "
The price is AU$404
includes taxes & fees
19 Oct - 20 Oct
210 Main St
Bar Harbor Main Street Apartments
Comfort Apartment, 2 Bedrooms, Kitchen | Living area

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 AU$774
includes taxes & fees
26 Oct - 27 Oct
Bar Harbor Main Street Apartments
House near Acadia National Park
Classic House | Living area

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 AU$786
includes taxes & fees
26 Oct - 27 Oct
House near Acadia National Park
Beautiful Apartments in Thorsen Road Maine
Comfort Apartment | Private kitchen

Beautiful Apartments in Thorsen Road Maine

3.0 star property
8.4 out of 10, Very good, (10)
"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. "
Beautiful Apartments in Thorsen Road Maine
Bar Harbor Condos
Suite A | Private kitchen

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 AU$507
includes taxes & fees
28 Oct - 29 Oct
Bar Harbor Condos
Downtown Apartments in Bar Harbor
Classic Apartment, 1 Queen Bed with Sofa bed, Kitchen | Living area

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 AU$794
includes taxes & fees
25 Oct - 26 Oct
Downtown Apartments in Bar Harbor
Genuine Farm experience! Barn loft on Organic Farm—pet pig and chickens below!
Exterior

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.
Outdoor spa tub

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 AU$596
includes taxes & fees
19 Oct - 20 Oct
Private And Cozy Tiny Home For Your Acadia Escape. Pet Friendly with Kayaks.
Private Indoor Pool Near Acadia National Park 25 mins from Bar Harbor
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (39)
"Fantastic house on a nice secluded side of the island. House was the perfect home base for all Acadia activities. The pool after a long day was a great way to wind down."
The price is AU$1,330
includes taxes & fees
19 Oct - 20 Oct
Private Indoor Pool Near Acadia National Park 25 mins from Bar Harbor
Charming Seaside Cottage with a Gas Fireplace, Spacious Patio, and Nearby Hiking
Interior

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
Perfectly Centered in Birch Harbor Village! Unit 4
Fridge, microwave, oven, stovetop

Perfectly Centered in Birch Harbor Village! Unit 4

10.0 out of 10, Exceptional, (43)
"I was very impressed with the spaciousness of this place. Very well appointed and super clean! I highly recommend staying there!"
Perfectly Centered in Birch Harbor Village! Unit 4
Historic 1940s lakeside cabin on spring-fed pond. Close to Acadia National Park
Interior

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

10.0 out of 10, Exceptional, (19)
"This was a wonderful place to stay, felt just like a summer camp! Cute cabin with a beautiful pond next to it for swimming/fishing/kayaking, etc. About 45 minutes from Acadia National Park, depending on what trail you're headed to."
Historic 1940s lakeside cabin on spring-fed pond. Close to Acadia National Park
Spectacular Ocean Views, Walking Distance To Town, Bike Into Acadia
Interior

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
Acadia Cabin 2 Cozy cabin with 1 bedroom and WiFi, AC
1 bedroom, WiFi, bed sheets

Acadia Cabin 2 Cozy cabin with 1 bedroom and WiFi, AC

2.0 star property
2.8 out of 10, (3)
"The stay was fine and the host a nice enough guy. However, just to lay out some facts: - The primary picture of the shed was taken before the units 1 and 2 were hung on the outside. The unit is half of that and you share a wall with another guest where you can hear everything they say or do. - The shed is about 50 yards from the primary house and about 50 feet from another structure that is an active construction site. - In order to turn on the AC, you have to stand on an old fold out wooden...
Acadia Cabin 2 Cozy cabin with 1 bedroom and WiFi, AC
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

Holiday Inn Resort Bar Harbor - Acadia Natl Park by IHG

Holiday Inn Resort Bar Harbor - Acadia Natl Park by IHG

10/10 Excellent
"This property has a jackpot of a view for Acadia! The back of this hotel is absolutely stunning! It a quick 4 minute drive into town for all the shopping and dining without having to be “in the chaos.” This is the second time we’ve stayed here and now it is newly renovated with beautiful rooms. The staff was also super helpful and accommodating for us with our baby. 10/10 this time! Highly recommend. No idea why it’s rated the way it is. I would tell all my friends to stay here just for the access to the waterfront and the view! "
Staci 7-night trip
Posted 14 hours ago
Holiday Inn Resort Bar Harbor - Acadia Natl Park by IHG

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 favourite 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 depend 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 AU$249 per night. Entering your travel dates in the search wizard might find you 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.