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

Holiday Homes in Winter Harbor

  • 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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Winter Harbor holiday homes

3 bedrooms, iron/ironing board, Internet, bed sheets

1. Pet-friendly Acadia basecamp: Hot Tub, EV Charger, Dual Kings & Trailer Parking

Pet-friendly Acadia basecamp: Hot Tub, EV Charger, Dual Kings & Trailer Parking
Ellsworth
The price is AU$1,150
includes taxes & fees
23 Aug - 24 Aug
Pet-friendly Acadia basecamp: Hot Tub, EV Charger, Dual Kings & Trailer Parking
House, Multiple Beds (Lazy Lumberjack Hilltop Cabin) | Living area

2. Lumberjack Cottages

Lumberjack Cottages
2.5 star property
Franklin
The price is AU$774
includes taxes & fees
3 Sept - 4 Sept
Lumberjack Cottages
Exterior

3. Water access house Acadia National Park Schoodic Point

Water access house Acadia National Park Schoodic Point
Gouldsboro
9.4 out of 10, Exceptional, (47 reviews)
"Everything we needed for a quick family weekend getaway!"
United States
Paul T.
The price is AU$824
includes taxes & fees
27 Aug - 28 Aug
Water access house Acadia National Park Schoodic Point
1 bedroom, bed sheets

4. Sun Shed Farm Stay

Sun Shed Farm Stay
Milbridge
8.6 out of 10, Excellent, (11 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 AU$158
includes taxes & fees
26 Aug - 27 Aug
Sun Shed Farm Stay
Terrace/patio

5. Cozy Milbridge Country Home

Cozy Milbridge Country Home
Milbridge
10.0 out of 10, Exceptional, (15 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 AU$392
includes taxes & fees
19 Aug - 20 Aug
Cozy Milbridge Country Home
Exterior

6. 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 AU$797
includes taxes & fees
1 Sept - 2 Sept
Tranquility by the Bay!
Property grounds

7. 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, (45 reviews)
"We had a lovely time and the host was great!"
United States
Anonymous traveller
The price is AU$2,016
includes taxes & fees
1 Sept - 2 Sept
Have an unforgettable getaway at a family sized beach house with private beach!
Beach

8. 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, (59 reviews)
"Such a cute house with lots of charm. Host was super responsive! We will definitely stay here again when we come back. "
United States
Staci D.
The price is AU$847
includes taxes & fees
13 Sept - 14 Sept
Booking now for summer & fall 2026-explore Acadia, Bar Harbor, Downeast Maine
Terrace/patio

9. Locally owned downtown home: Bar Harbors Crows' Nest

Locally owned downtown home: Bar Harbors Crows' Nest
Downtown Bar Harbor
10.0 out of 10, Exceptional, (74 reviews)
"A perfect spot for our family and friends. All stocked, even with baby friendly items. Location is perfect close to all downtown walking and the ocean. Margie is fantastic! Easy check in, comfortable house and space. We hope to go back again sometime!"
United States
Kelly M.
The price is AU$1,104
includes taxes & fees
12 Sept - 13 Sept
Locally owned downtown home: Bar Harbors Crows' Nest
Smart TV, DVD player, books, music library

10. Mullein Hill Cottage: Escape Crowds to MDI’s Quiet, Historic Birthplace

Mullein Hill Cottage: Escape Crowds to MDI’s Quiet, Historic Birthplace
Somesville
Mullein Hill Cottage: Escape Crowds to MDI’s Quiet, Historic Birthplace
Smart TV, DVD player, books

11. 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, (15 reviews)
"Cute house. Great area. "
United States
Karren Y.
The price is AU$914
includes taxes & fees
19 Aug - 20 Aug
Charming 2-bedroom house with WiFi, AC in Southwest Harbor
Exterior detail

12. The Colonels Suites

The Colonels Suites
2.0 star property
Northeast Harbor
The price is AU$793
includes taxes & fees
19 Aug - 20 Aug
The Colonels Suites
Terrace/patio

13. Acadia View Cottage: Peaceful, Pet Friendly, Fire Pit, Near Peaks and Echo Lake

Acadia View Cottage: Peaceful, Pet Friendly, Fire Pit, Near Peaks and Echo Lake
Hall Quarry
10.0 out of 10, Exceptional, (2 reviews)
"Great stay for a weekend hiking getaway with friends! The house was clean and nicely renovated. The beds were comfortable and the AC in all the upstairs bedrooms were great for cooling the house. The free snacks and coffee were a delightful surprise! There was easy car access to the main entrance to Acadia. The neighborhood was quiet and we enjoyed the evenings at the fire pit. It’s definitely a go-to place for our group the next time we are at Acadia!"
United States
Tanishia C.
The price is AU$1,051
includes taxes & fees
31 Aug - 1 Sept
Acadia View Cottage: Peaceful, Pet Friendly, Fire Pit, Near Peaks and Echo Lake
TV, DVD player, books

14. 13 Mi to Acadia: Artistic Retreat in Nature

13 Mi to Acadia: Artistic Retreat in Nature
Trenton
9.6 out of 10, Exceptional, (9 reviews)
"We booked very last minute at this place. It’s very quirky but comfortable! "
United States
Katie P.
The price is AU$753
includes taxes & fees
25 Aug - 26 Aug
13 Mi to Acadia: Artistic Retreat in Nature
TV

15. Wildwood Cottage at Gallagher`s Travels

Wildwood Cottage at Gallagher`s Travels
Bar Harbor
9.4 out of 10, Exceptional, (3 reviews)
"Friendly, helpful, responsive host. Nice property conveniently located. We had a great stay!"
United States
Andrea C.
The price is AU$843
includes taxes & fees
31 Aug - 1 Sept
Wildwood Cottage at Gallagher`s Travels
Coffee/tea maker, fridge, microwave, oven

16. Acadia Retreat- 3 bedroom, 2 bath on two private serene acres

Acadia Retreat- 3 bedroom, 2 bath on two private serene acres
Lamoine
10.0 out of 10, Exceptional, (8 reviews)
"Property was very clean, comfortable, and great location with a short drive to Acadia National Park."
United States
Eddie G.
Acadia Retreat- 3 bedroom, 2 bath on two private serene acres
Interior

17. Spacious Seven Peaks Ridge: Quiet Side Hot Tub, Pet Friendly, Fire Pit & Deck

Spacious Seven Peaks Ridge: Quiet Side Hot Tub, Pet Friendly, Fire Pit & Deck
Southwest Harbor
10.0 out of 10, Exceptional, (4 reviews)
"Very convenient access to Acadia Enjoyed hot tub Beautiful night sky Ideal for 6"
United States
Malisha D.
The price is AU$1,408
includes taxes & fees
2 Sept - 3 Sept
Spacious Seven Peaks Ridge: Quiet Side Hot Tub, Pet Friendly, Fire Pit & Deck
Smart TV, fireplace, books

18. Quietside Quarterdeck: Dual King Wings, Bunk Room, Fire Patio & Pet-Friendly

Quietside Quarterdeck: Dual King Wings, Bunk Room, Fire Patio & Pet-Friendly
Southwest Harbor
10.0 out of 10, Exceptional, (6 reviews)
The price is AU$1,070
includes taxes & fees
31 Aug - 1 Sept
Quietside Quarterdeck: Dual King Wings, Bunk Room, Fire Patio & Pet-Friendly
Exterior detail

19. Efficient Getaway with Free WiFi - Close to Acadia National Park

Efficient Getaway with Free WiFi - Close to Acadia National Park
Northeast Harbor
8.4 out of 10, Very good, (24 reviews)
"Nice place"
United States
Eric D.
Efficient Getaway with Free WiFi - Close to Acadia National Park
TV

20. House Acadia at Gallagher`s Travels

House Acadia at Gallagher`s Travels
Bar Harbor
9.8 out of 10, Exceptional, (7 reviews)
"Bathroom need to be upgrades"
United States
Bhikhabhai
The price is AU$1,058
includes taxes & fees
24 Aug - 25 Aug
House Acadia at Gallagher`s Travels
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

Kimball Terrace Inn Northeast Harbor

Kimball Terrace Inn Northeast Harbor

10/10 Excellent
"The rooms were large and clean. The staff very nice and answered any questions we had. We ate several times at the attached restaurant and had drinks at the bar. The service there was also really good. The food was delicious. Parking was easy and we could walk right to town to shop and eat. They also have a cute little gift shop in the lobby that we shop that and bought some items from."
Kimberly 3-night trip
Posted 7 hours ago
Kimball Terrace Inn Northeast Harbor

Find out more about Winter Harbor

Winter Harbor Holiday Homes information

Number of reviews
326
Accommodation
856 Holiday Homes
Lowest Price
AU$158
Highest Price
AU$2,016