Winter Harbor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winter Harbor holiday rentals

Courtyard

Cottage in Bar Harbor

Hanscom's Motel and Cottages
3.0 star property
9.4 out of 10, Exceptional, (321 reviews)
"Room was so clean and charming! Beautifully decorated and quite cozy! Will stay here again. "
United States
Lori
The price is HK$796
HK$867 total
includes taxes & fees
19 Jan - 20 Jan
Hanscom's Motel and Cottages
Outdoor dining

Apartment in Trenton

16 Apartment near Acadia Open Hearth Inn
9.2 out of 10, Wonderful, (17 reviews)
"Great location and communication!"
United States
Megan L.
The price is HK$491
HK$833 total
includes taxes & fees
20 Jan - 21 Jan
16 Apartment near Acadia Open Hearth Inn
Outdoor dining

Apartment in Trenton

15 1Br Cottage Heart of Maine Open Hearth Inn
9.6 out of 10, Exceptional, (19 reviews)
"Nice little place to stay. We would stay again."
United States
Rick & Jill A.
The price is HK$491
HK$833 total
includes taxes & fees
19 Jan - 20 Jan
15 1Br Cottage Heart of Maine Open Hearth Inn
Interior

Apartment in Trenton

5 Suite in 1820`s house Open Hearth Inn
10.0 out of 10, Exceptional, (9 reviews)
"Excellent place to stay. "
United States
ANITA
The price is HK$491
HK$833 total
includes taxes & fees
19 Jan - 20 Jan
5 Suite in 1820`s house Open Hearth Inn
Interior

Apartment in Trenton

1 Lovely Suite in Bar Harbor Open Hearth Inn
10.0 out of 10, Exceptional, (13 reviews)
"Friendly, helpful staff, clean well stocked kitchen, comfortable and fun place. Our small dog absolutely loved it there and even fell in love with a French bulldog! Good proximity to Acadia NP and Bar Harbor. Highly recommend!"
United States
Alexandra D.
The price is HK$491
HK$833 total
includes taxes & fees
19 Jan - 20 Jan
1 Lovely Suite in Bar Harbor Open Hearth Inn
Property grounds

Apartment in Trenton

Isleview Gallery Rm 11 - Walk to lobster shacks!
9.4 out of 10, Exceptional, (3 reviews)
"This was a small room. Fine for one person, but could be a nuisance for a pair if they have significant luggage. The shower is cramped. Easy to get in. I didn't initially realize there were more supplies in the office downstairs (soap, creamer, etc.). There is also a general store & gas less than a mile to the west. The location is a bit further from both Acadia and Bar Harbor than most options, but not significantly so where you'd have to really plan for extra time to get anywhere. The nearby...
United States
Philip C.
The price is HK$491
HK$833 total
includes taxes & fees
19 Jan - 20 Jan
Isleview Gallery Rm 11 - Walk to lobster shacks!
Interior

Apartment in Trenton

18 Acadia Lodge King Bed AC Open Hearth Inn
9.4 out of 10, Exceptional, (17 reviews)
"Exactly what I was looking for and even better than described. "
United States
Jerl B.
The price is HK$491
HK$833 total
includes taxes & fees
19 Jan - 20 Jan
18 Acadia Lodge King Bed AC Open Hearth Inn
Fitness facility

Aparthotel in Ellsworth

Stone Park
4.0 star property
9.2 out of 10, Wonderful, (189 reviews)
"Very clean and quiet, friendly staff. Excellent place to stay"
United States
John
The price is HK$975
HK$1,063 total
includes taxes & fees
19 Jan - 20 Jan
Stone Park
Exterior

Holiday Home in Gouldsboro

Water access house Acadia National Park Schoodic Point
9.4 out of 10, Exceptional, (38 reviews)
"Property just as described, we really enjoyed our stay. "
United States
Ross A.
The price is HK$877
HK$2,528 total
includes taxes & fees
19 Jan - 20 Jan
Water access house Acadia National Park Schoodic Point
Outdoor dining

Apartment in Trenton

11 Cute 1Br Acadia Cottage Open Hearth Inn
9.6 out of 10, Exceptional, (5 reviews)
"This was the perfect spot for us and the dogs! Everyone was so friendly, perfect location, and super clean! Would love to stay here again next time we are in town!"
United States
Meredith T.
The price is HK$491
HK$833 total
includes taxes & fees
19 Jan - 20 Jan
11 Cute 1Br Acadia Cottage Open Hearth Inn
Interior

Apartment in Trenton

19 Acadia Lodge Sleeps 4 Open Hearth Inn
8.8 out of 10, Excellent, (16 reviews)
"Our room was really nice, and very welcoming. Would definitely stay again."
United States
Cherie
The price is HK$491
HK$833 total
includes taxes & fees
19 Jan - 20 Jan
19 Acadia Lodge Sleeps 4 Open Hearth Inn
Private kitchen

Holiday Home in Ellsworth

Deer Ridge A/C, Firepit, Pool Table, Acadia
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house in a great location "
United States
Alicia H.
The price is HK$795
HK$2,592 total
includes taxes & fees
31 Jan - 1 Feb
Deer Ridge A/C, Firepit, Pool Table, Acadia
Smart TV, fireplace, books, stereo

Cottage in Steuben

Downeast Maine Cottage with Water View and Nature Preserve
10.0 out of 10, Exceptional, (16 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 HK$1,123
HK$3,476 total
includes taxes & fees
20 Jan - 21 Jan
Downeast Maine Cottage with Water View and Nature Preserve
Interior

Holiday Home in Ellsworth

Oceanfront Maine Retreat-Mins to Acadia/Bar Harbor
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The hosts were very helpful, responsive and accommodating. The property is very well appointed, beautifully decorated and in an amazing location...the scenery is stunning. "
United States
Jayne G.
The price is HK$929
HK$2,840 total
includes taxes & fees
20 Jan - 21 Jan
Oceanfront Maine Retreat-Mins to Acadia/Bar Harbor
Living area

Holiday Home in Ellsworth

Harbor ViewCharming 3-bedroom house in delightful Acadia Area AC, WiFi
9.6 out of 10, Exceptional, (5 reviews)
"Great place to see all that Acadia National Park has to offer."
United States
David G.
The price is HK$795
HK$2,694 total
includes taxes & fees
23 Jan - 24 Jan
Harbor ViewCharming 3-bedroom house in delightful Acadia Area AC, WiFi
1 bedroom, premium bedding, free WiFi, bed sheets

Aparthotel in Bar Harbor

Bar Harbor Condos
2.5 star property
10.0 out of 10, Exceptional, (10 reviews)
"Walked in to an immaculately clean place to stay for a night in Bar Harbor. Had everything we were looking for. We’ll definitely book with Tim and Eric again!"
United States
Brad
The price is HK$778
HK$849 total
includes taxes & fees
19 Jan - 20 Jan
Bar Harbor Condos
Interior

Cottage in Tremont

Blue Lobster Cottage in brilliant Acadia with AC, WiFi
8.8 out of 10, Excellent, (3 reviews)
"Location is quiet and not too far from Acadia. Minor issue with the attention to detail on cleaning as the blankets on couch and sheets for pull out couch were not clean. I emailed host and no response, either. "
United States
Rachel
The price is HK$764
HK$2,558 total
includes taxes & fees
20 Jan - 21 Jan
Blue Lobster Cottage in brilliant Acadia with AC, WiFi
Smart TV

Cottage in Southwest Harbor

Red Finn Cottage@ ACADIA NATIONAL PARK
8.0 out of 10, Very good, (8 reviews)
"Definitely recommend to those looking for a place to stay in the Acadia/bar harbor area! Very cute and clean and had everything we needed. Even snacks (:"
United States
Emily D.
The price is HK$694
HK$2,422 total
includes taxes & fees
21 Jan - 22 Jan
Red Finn Cottage@ ACADIA NATIONAL PARK
Beach

Holiday Home in Lamoine

Secluded Bungalow Near Acadia & Bar Harbor - Private- Pet Friendly- Heated Pool- Huge Yard
9.6 out of 10, Exceptional, (4 reviews)
"Very clean, comfortable, peaceful"
United States
Cassandra D.
The price is HK$783
HK$2,696 total
includes taxes & fees
19 Jan - 20 Jan
Secluded Bungalow Near Acadia & Bar Harbor - Private- Pet Friendly- Heated Pool- Huge Yard
1 bedroom, WiFi, bed sheets

Apartment in Gouldsboro

Cozy studio with spectacular views of Bunker's Harbor in Birch Harbor!
10.0 out of 10, Exceptional, (5 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 HK$1,403
HK$1,972 total
includes taxes & fees
20 Jan - 21 Jan
Cozy studio with spectacular views of Bunker's Harbor in Birch 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Harbor Hotel Reviews

The Pathmaker Hotel

The Pathmaker Hotel

10/10 Excellent
"Absolutely in LOVE with this hotel, rooms and restaurant! Very chic, clean, amazing customer service checking in and out! Cant say enough great things about the included breakfast 😋 so delicious! Definitely going back for a summer stay in Bar Harbor!"
Maria 2-night trip
Posted 2 days ago
The Pathmaker Hotel

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
  • Use the map to find apartments and other holiday homes in the Winter Harbor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Harbor while they last

Look no further and take a look at our great range of rental properties in Winter Harbor!

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?

Luxury Home w/INDOOR POOL 20mins BarHarbor boardersAcadia National Par: This holiday home rental outside of Winter Harbor is located in a rural location, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.