Photo by Ricky Batista

Winter Harbor Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Winter Harbor

Hanscom's Motel and Cottages
3.0 star property
9.2 out of 10, Wonderful, (219)
"The unit was modern, extremely clean. Community fire pits stocked with plenty of wood just bring your own marshmallows 😎. We loved the communication. We received a welcome text the day before our visit and a text the day of our visit with the room code so there was no check in required. "
The price is S$182
includes taxes & fees
24 Nov - 25 Nov
Hanscom's Motel and Cottages
Lighthouse Cabins Maine
3.0 star property
10.0 out of 10, Exceptional, (91)
"Property was very nice and clean. Just 3 cabins on site so a small establishment. The owner/manger seemed nice. There were pastries etc for breakfast but we had bagels with us which we toasted in the toaster in the cabin and had with some nice hot coffee. The roon was mostly well appointed. The bed was a bit soft for us but others may like it. Best part is you can walk to the lighthouse which makes great sense during sunset times. "
Lighthouse Cabins Maine
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.
Don't see what you're looking for?
See all available properties in Winter Harbor
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Winter Harbor you may be interested in

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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.

How many holiday rentals are there in Winter Harbor?

Expedia has 15 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.