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Top Holiday Rentals in Winter Harbor

Waterfront Home on Private Island with HOT TUB

9.2 out of 10, Wonderful, (7)
"Great House Great walking area, nice town Beautiful Hot Tub Quiet"
The price is £791
includes taxes & fees
24 Jul - 25 Jul
Waterfront Home on Private Island with HOT TUB

Private, quiet & beautiful second story with peek a boo water views

10.0 out of 10, Exceptional, (28)
"We really enjoyed our stay here. The properly was immaculately clean which made us feel very comfortable. We enjoyed the spacious and roomy feel and took advantage of the fantastic kitchen which had all the equipment to cook as we wished. We would highly recommend this property and the host, who was very helpful and a pleasure to deal with."
The price is £224
includes taxes & fees
30 Jun - 1 Jul
Private, quiet & beautiful second story with peek a boo water views

Cozy Milbridge retreat just steps away

9.8 out of 10, Exceptional, (9)
"This was a great little house. It had everything we could need and more. Everything was clean, the bed was comfortable, the Roku TVs work included HBO Max in living room and bedroom were a nice touch too."
The price is £194
includes taxes & fees
30 Jun - 1 Jul
Cozy Milbridge retreat just steps away

Sun Shed Farm Stay

8.0 out of 10, Very good, (4)
"Very welcoming hosts. Take the farm tour if you have the chance, lots of beautiful animals to meet! Sun shed is cozy and well-kept. "
The price is £73
includes taxes & fees
27 Jul - 28 Jul
Sun Shed Farm Stay

Large, secluded home with beautiful private stone beach to explore!

10.0 out of 10, Exceptional, (28)
"Enjoyed the home and location. Great for our family and a good layout. Thank Mother Nature for perfect weather!"
The price is £1,337
includes taxes & fees
28 Jun - 29 Jun
Large, secluded home with beautiful private stone beach to explore!

Cozy studio with spectacular views of Bunker's Harbor in Birch Harbor!

10.0 out of 10, Exceptional, (1)
The price is £166
includes taxes & fees
7 Jul - 8 Jul
Cozy studio with spectacular views of Bunker's Harbor in Birch Harbor!

Water access house Acadia National Park Schoodic Point

9.0 out of 10, Wonderful, (24)
"We had a great time at this property. The host was friendly and helpful and the amenities provided were excellent."
The price is £415
includes taxes & fees
22 Jul - 23 Jul
Water access house Acadia National Park Schoodic Point

Bike, hike, kayak Acadia cottage

The price is £390
includes taxes & fees
25 Jul - 26 Jul
Bike, hike, kayak Acadia cottage

Deluxe King Room w/ Breakfast Included

10.0 out of 10, Exceptional, (27)
"Easy communication and great location, definitely will be coming back! "
The price is £270
includes taxes & fees
6 Jul - 7 Jul
Deluxe King Room w/ Breakfast Included

4-bedroom house in charming Southwest Harbor with short walk to Seawall

The price is £465
includes taxes & fees
1 Jul - 2 Jul
4-bedroom house in charming Southwest Harbor with short walk to Seawall

Efficient Getaway with Free WiFi - Close to Acadia National Park

8.6 out of 10, Excellent, (21)
"Nice place"
The price is £311
includes taxes & fees
28 Jun - 29 Jun
Efficient Getaway with Free WiFi - Close to Acadia National Park

Downtown suite near with water with central AC and shared washer/dryer

9.0 out of 10, Wonderful, (17)
"The location is fantastic and the apartment was perfect. Loved the ability to walk everywhere and proximity to the water!"
The price is £342
includes taxes & fees
28 Jun - 29 Jun
Downtown suite near with water with central AC and shared washer/dryer

Southwest Harbor Cottage steps away the Ocean and Acadia National Park

9.8 out of 10, Exceptional, (111)
"Beautiful house. Great location"
The price is £554
includes taxes & fees
29 Jun - 30 Jun
Southwest Harbor Cottage steps away the Ocean and Acadia National Park

Gallaghers Travels Room 12-A (King)

10.0 out of 10, Exceptional, (1)
"We LOVE this motel! Very clean, the bed was SO comfortable and the people are so nice and accommodating. Thank you for a great stay :) 10/10"
The price is £177
includes taxes & fees
29 Jun - 30 Jun
Gallaghers Travels Room 12-A (King)

Gallaghers Travels Room 9

8.0 out of 10, Very good, (1)
"Location location location!!! A literal 3 minute drive to the Acadia park entrance and 10 minutes down the road from bar harbor. Makes the 4am drive for Cadillac mountain sunrise so much easier. I’ve stayed in many places right next to National parks (most being run down but can’t beat the location) and this was by far one of the comfiest. Would absolutely stay again"
The price is £188
includes taxes & fees
29 Jun - 30 Jun
Gallaghers Travels Room 9

Gallagher's Travels Cabin Three (Queen)

10.0 out of 10, Exceptional, (1)
"Just went to see the area while visiting my son at UMaine "
The price is £273
includes taxes & fees
6 Jul - 7 Jul
Gallagher's Travels Cabin Three (Queen)

Gallagher's Travels Room Ten (Queen)

10.0 out of 10, Exceptional, (1)
"The room was clean and well taken care of and the location was perfect for me! Minutes from Acadia and Bar Harbor."
The price is £227
includes taxes & fees
27 Jul - 28 Jul
Gallagher's Travels Room Ten (Queen)

Gallagher's Travels Room Fourteen (Double Queen)

The price is £245
includes taxes & fees
10 Jul - 11 Jul
Gallagher's Travels Room Fourteen (Double Queen)

Gallagher's Travels Room 15 (King Suite)

The price is £230
includes taxes & fees
29 Jun - 30 Jun
Gallagher's Travels Room 15 (King Suite)

Gallagher's Travels Cabin One (Single Queen)

The price is £249
includes taxes & fees
7 Jul - 8 Jul
Gallagher's Travels Cabin One (Single Queen)
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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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 16 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.