Winter Harbor Vacation Rentals

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Make Winter Harbor your next getaway

Explore our vacation rentals in Winter Harbor, ME. Our private accommodations include everything you need to have the perfect getaway, whether you're here for a family vacation, couples retreat, or making memories with friends.

Explore Winter Harbor house rentals, and more

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House rentals

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Winter Harbor vacation rentals for every getaway

Popular
Internet Lake view Ocean view
Coastal Maine Attraction

Coastal Maine Attraction

House in Winter Harbor

$622 avg / night

4.5 (6)

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Listings nearby Winter Harbor

Pom Cottage

Pom Cottage

House in Prospect Harbor

$1,307 avg / night

Aril Cottage

Aril Cottage

Bungalow in Prospect Harbor

$795 avg / night

Cadillac Mountain Overlook

Cadillac Mountain Overlook

House in Bar Harbor

$1,722 avg / night

4.97 (36)
Birdsong Carriage House

Birdsong Carriage House

House in Bar Harbor

$786 avg / night

5.0 (1)

Vacation rentals near Winter Harbor

Explore more vacation rental amenities in Winter Harbor

Water view
Waterfront
A/C
Air conditioning
Fireplace
Washer/dryer
Balcony
Bikes
Golf on-site
Ping-pong table

Recent Winter Harbor vacation rental reviews

Close to Schoodic Peninsula of Acadia National Park. Easily accessed and absolutely beautiful. Great restaurants nearby and very quiwt
Charles B. | Oct 2025
Maine Attraction was perfect for our trip to Winter Harbor. We loved being able to walk to restaurants, shops, and the waterfront. This adorable cottage had everything we needed and is so charming and cozy; very clean, beds were very comfortable. I would give it more than 5 stars if I could. Highly recommend!
Martha K. | Sep 2025
Home is exactly as listed. Great to spend a day in Schoodic and avoid crowded Bar Harbor.
Madalyn P. | Aug 2025
We loved the location in Winter Harbor. Close to lots of great places and it was nice and quiet. Would definitely stay here again!
Susan B. | Aug 2025
Winter Harbor Frequently Asked Questions

Yes. 44 of our Winter Harbor vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Winter Harbor vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Winter Harbor team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Winter Harbor, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

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