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

Holiday Homes in Winter Harbor

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winter Harbor holiday homes

Outdoor dining

1. Take in the breathtaking views at our popular oceanside cottage with large deck.

Take in the breathtaking views at our popular oceanside cottage with large deck.
Gouldsboro
9.8 out of 10, Exceptional, (59 reviews)
"Great place in a beautiful location!"
United States
Laura B.
The price is NZ$1,116
includes taxes & fees
19 Oct - 20 Oct
Take in the breathtaking views at our popular oceanside cottage with large deck.
Exterior

2. Water access house Acadia National Park Schoodic Point

Water access house Acadia National Park Schoodic Point
Gouldsboro
9.2 out of 10, Wonderful, (53 reviews)
"The house was comfortable and clean. We enjoyed the fire pit and charcoal grill. Jeff was very friendly and helpful. The location was wonderful for exploring Acadia and especially the Schoodic Peninsula."
United States
Linette
The price is NZ$1,006
includes taxes & fees
1 Oct - 2 Oct
Water access house Acadia National Park Schoodic Point
Exterior

3. Tranquility by the Bay!

Tranquility by the Bay!
Steuben
9.4 out of 10, Exceptional, (3 reviews)
"Clean, comfortable - everything we needed. Loved the screened in porch and the coffee provided was a nice touch. Huge bathroom. Excellent AC! Would love to stay again."
United States
Amy K.
The price is NZ$711
includes taxes & fees
23 Sept - 24 Sept
Tranquility by the Bay!
Terrace/patio

4. Cozy Milbridge Country Home

Cozy Milbridge Country Home
Milbridge
10.0 out of 10, Exceptional, (16 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$470
includes taxes & fees
25 Sept - 26 Sept
Cozy Milbridge Country Home
Property grounds

5. Have an unforgettable getaway at a family sized beach house with private beach!

Have an unforgettable getaway at a family sized beach house with private beach!
Steuben
10.0 out of 10, Exceptional, (47 reviews)
"We had a lovely time and the host was great!"
United States
Anonymous traveller
The price is NZ$2,078
includes taxes & fees
25 Sept - 26 Sept
Have an unforgettable getaway at a family sized beach house with private beach!
1 bedroom, bed sheets

6. Sun Shed Farm Stay

Sun Shed Farm Stay
Milbridge
8.6 out of 10, Excellent, (12 reviews)
"Fun way to get off the beaten track, enjoyed waking up to some farm animals nearby, and the stars were incredible."
United States
Matthew
The price is NZ$192
includes taxes & fees
23 Sept - 24 Sept
Sun Shed Farm Stay
Exterior

7. Blueberry Basecamp: 98ft to Acadia! Hike from Home, AC, Deck, Near Bar Harbor

Blueberry Basecamp: 98ft to Acadia! Hike from Home, AC, Deck, Near Bar Harbor
Otter Creek
10.0 out of 10, Exceptional, (2 reviews)
"House is the perfect place to stay on MDI for any itinerary. Location cant be beat- close to Bar Harbor yet so quiet at the end of a charming dead end road. House is so clean, comfortable, and newly renovated. Great new baths, beds, deck and thoroughly equipped kitchen. Will absolutely stay again!"
United States
John S.
The price is NZ$1,374
includes taxes & fees
23 Sept - 24 Sept
Blueberry Basecamp: 98ft to Acadia! Hike from Home, AC, Deck, Near Bar Harbor
TV

8. Great Harbor Inn Clarks Quarters

Great Harbor Inn Clarks Quarters
Southwest Harbor
8.0 out of 10, Very good, (3 reviews)
"Thanks. We enjoyed our time."
United States
Ed L.
The price is NZ$533
includes taxes & fees
22 Oct - 23 Oct
Great Harbor Inn Clarks Quarters
Exterior detail

9. The Colonels Suites

The Colonels Suites
2.0 star property
Northeast Harbor
The price is NZ$683
includes taxes & fees
13 Oct - 14 Oct
The Colonels Suites
Exterior

10. Cozy Cottage Surrounded by Acadia National Park

Cozy Cottage Surrounded by Acadia National Park
Somesville
The price is NZ$909
includes taxes & fees
22 Oct - 23 Oct
Cozy Cottage Surrounded by Acadia National Park
Terrace/patio

11. Carriage House - Crocker House Country Inn

Carriage House - Crocker House Country Inn
Hancock Point
8.8 out of 10, Excellent, (3 reviews)
"The overall space is definitely rustic. Staff is very friendly and the breakfast we had was tasty. Lots of parking for the most part, except at dinner time when the restaurant is open. The one issue we had was we stayed in the carriage house. Which you cannot lock the main door too which is fine if the front desk tells you that. Unfortunately they didn’t tell us and we were locked out for about 30m till we figured out a way into the space. There is no night staff at all so you are on your own if...
United States
Gina C.
The price is NZ$633
includes taxes & fees
30 Sept - 1 Oct
Carriage House - Crocker House Country Inn
Beach

12. 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, (60 reviews)
"Holly was communicative and assisted whenever needed. The property was amazing, it was clean and plenty of space, I’d love to come back again."
United States
Rowan W.
The price is NZ$1,074
includes taxes & fees
27 Sept - 28 Sept
Booking now for summer & fall 2026-explore Acadia, Bar Harbor, Downeast Maine
Beach nearby, sun-loungers, beach towels

13. Quiet location. Home is 1/2 a mile to Seawall Beach and 3 miles to town center.

Quiet location. Home is 1/2 a mile to Seawall Beach and 3 miles to town center.
Seawall
10.0 out of 10, Exceptional, (171 reviews)
"Excellent location—close to Acadia and Bar Harbor. This was such a comfortable house to go back to after full days in the Park. So clean, fully stocked kitchen, laundry machines, comfortable beds and living room, nice towels…We highly recommend this place!"
United States
Teresa B.
The price is NZ$914
includes taxes & fees
15 Oct - 16 Oct
Quiet location. Home is 1/2 a mile to Seawall Beach and 3 miles to town center.
Beach

14. Secluded Bungalow Near Acadia & Bar Harbor - Private- Pet Friendly

Secluded Bungalow Near Acadia & Bar Harbor - Private- Pet Friendly
Lamoine
9.6 out of 10, Exceptional, (5 reviews)
"Very clean, comfortable, peaceful"
United States
Cassandra D.
The price is NZ$998
includes taxes & fees
23 Sept - 24 Sept
Secluded Bungalow Near Acadia & Bar Harbor - Private- Pet Friendly
Smart TV, DVD player, books

15. Charming 2-bedroom house with WiFi, AC in Southwest Harbor

Charming 2-bedroom house with WiFi, AC in Southwest Harbor
Southwest Harbor
9.6 out of 10, Exceptional, (16 reviews)
"Comfortable cottage in quiet neighborhood. Well stocked, and great amenities. Had a wonderful time exploring Acadia and the surrounding area."
United States
Eric W.
The price is NZ$1,051
includes taxes & fees
26 Sept - 27 Sept
Charming 2-bedroom house with WiFi, AC in Southwest Harbor
TV

16. House Acadia at Gallagher`s Travels

House Acadia at Gallagher`s Travels
Bar Harbor
9.8 out of 10, Exceptional, (7 reviews)
"Great communication with host. The location was perfect for our needs. Overall great place"
United States
Hunter H.
The price is NZ$831
includes taxes & fees
27 Sept - 28 Sept
House Acadia at Gallagher`s Travels
Coffee/tea maker, fridge, microwave, oven

17. Acadia: Birch Tree Hollow

Acadia: Birch Tree Hollow
Trenton
10.0 out of 10, Exceptional, (1 review)
"It was a great location for our multi-generational family vacation-- a short car ride to the Hull Cove Visitor Center in Acadia National Park. The street was a quiet private road. Our granddaughters and grand-dog had room to romp and play. Well stocked, well maintained and tastefully appointed.Everything about the home was perfect for us!"
United States
Elaine C.
Acadia: Birch Tree Hollow
Smart TV

18. Hadley Point Hideaway, Quiet & Peaceful

Hadley Point Hideaway, Quiet & Peaceful
Bar Harbor
10.0 out of 10, Exceptional, (5 reviews)
"Hadley Point Hideaway was the perfect place for my wife, son and me to spend our Bar Harbor vacation! Close to everything, but far enough to be out of the touristy areas! We loved hiking through Acadia and enjoyed the great restaurants! We would definitely stay here again and highly recommend this great VRBO experience!!!"
United States
Robert C.
The price is NZ$849
includes taxes & fees
20 Oct - 21 Oct
Hadley Point Hideaway, Quiet & Peaceful
House, Multiple Beds (Lazy Lumberjack Hilltop Cabin) | Living area

19. Lumberjack Cottages

Lumberjack Cottages
2.5 star property
Franklin
The price is NZ$858
includes taxes & fees
24 Sept - 25 Sept
Lumberjack Cottages
Family House | Private kitchen

20. Beautiful Bar Harbor House

Beautiful Bar Harbor House
4.0 star property
Bar Harbor
The price is NZ$1,799
includes taxes & fees
19 Oct - 20 Oct
Beautiful Bar Harbor House
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

Comfort Inn Ellsworth - Bar Harbor

Comfort Inn Ellsworth - Bar Harbor

8/10 Good
"Pictures hanging on walls in hallway 2nd floor were crooked and looked old, cheap. Don't need to have lots of decor setting out. Less is better. Carpet on stairs dirty. Need healthier options for breakfast. Offer hot oatmeal already on crockpot. Milk should not be in container. Needs to be in refrigerator. Greek yogurt would be better."
Raquel 3-night trip
Posted less than an hour ago
Comfort Inn Ellsworth - Bar Harbor

Find out more about Winter Harbor

Winter Harbor Holiday Homes information

Number of reviews
Accommodation
920 Holiday Homes
Lowest Price
NZ$683
Highest Price
NZ$1,799