Photo by Linda Kloss

Winterport Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 22 - Aug 24
Next weekend
Aug 29 - Aug 31

Vacation Rentals in Winterport

1812 Pierce House
Front of property

1812 Pierce House

3.5 star property
1812 Pierce House
Cozy 2 BR by River- Crooked Steeple Hall
Signature House, 2 Bedrooms, Patio, River View | Private kitchen | Fridge, microwave, oven, stovetop

Cozy 2 BR by River- Crooked Steeple Hall

4.0 star property
Cozy 2 BR by River- Crooked Steeple Hall
35 Mi to Acadia: Rustic Retreat in Orland!
House (1 Bedroom) | Interior

35 Mi to Acadia: Rustic Retreat in Orland!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Exactly what you think of a cabin in the Maine woods. Close to Bucksport. No wifi. Only got one channel on the rabbit ears for the TV, but many movies available to use on the dvd player. Dark outside at night. Quick response from property manager. Would stay there again. "
35 Mi to Acadia: Rustic Retreat in Orland!
Waterfront Hampden Home on Hermon Pond!
House (3 Bedrooms) | Interior

Waterfront Hampden Home on Hermon Pond!

3.0 star property
8.0 out of 10, Very Good, (2)
"A beautiful and quiet spot on the water, only a few miles from town. We heard loons and saw a bald eagle grab a fish from the pond. The house itself was cozy, clean, and comfortable. "
Waterfront Hampden Home on Hermon Pond!
Secluded Orland Cottage w/ Grill, Near State Parks
Cottage (2 Bedrooms) | Interior

Secluded Orland Cottage w/ Grill, Near State Parks

3.0 star property
Secluded Orland Cottage w/ Grill, Near State Parks
Pet-friendly Prospect Apartment: 7 Mi to Beach!
Apartment (1 Bedroom) | Interior

Pet-friendly Prospect Apartment: 7 Mi to Beach!

3.0 star property
7.0 out of 10, Good, (2)
"Like: Very private, close to nature, extra blankets available, very clean kitchen and bathroom, towels and cafe k-cups available Didn't like: Mattress, odor in the bathroom, yellow pillow under pillowcase"
Pet-friendly Prospect Apartment: 7 Mi to Beach!
Pet-friendly Ellsworth Cottage on Branch Lake
Cottage (1 Bedroom) | Interior

Pet-friendly Ellsworth Cottage on Branch Lake

3.0 star property
Pet-friendly Ellsworth Cottage on Branch Lake
Rustic Searsport Cabin: Loft + Sunroom on 10 Acres
House (2 Bedrooms) | Interior

Rustic Searsport Cabin: Loft + Sunroom on 10 Acres

3.0 star property
10.0 out of 10, Exceptional, (3)
"This cabin is very well decorated with comfortable bedding and furniture. The decor and taxidermy are consistent with a rustic cabin, while the kitchen is set up well to cook, with all the condiments and seasonings to be able to eat in if you choose. The cabin and the nearby hosts both exceeded expectations."
Rustic Searsport Cabin: Loft + Sunroom on 10 Acres
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winterport Hotel Reviews

Bangor Aviator Hotel, BW Premier Collection

Bangor Aviator Hotel, BW Premier Collection

10/10 Excellent
"This was a perfect solution for stay before an early morning flight. So easy to walk right over to the airport and the hotel restaurant was excellent!"
Christine 1-night trip
Posted 1 day ago
Bangor Aviator Hotel, BW Premier Collection

Frequently asked questions

Are there vacation rentals in Winterport?

Yes, there are vacation rentals near popular local attractions in Winterport, or you can select a secluded option if you'd like a relaxing place to stay. Winterport is known for its shopping and restaurants. Make sure you have time to check out the wineries while you're in the area.

What are some of the best vacation home rentals in Winterport?

1812 Pierce House: This Winterport vacation home rental is equipped with a barbecue grill, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Our travelers also rate Cozy 2 BR by River- Crooked Steeple Hall as a favorite home for rent in Winterport.

How many vacation rentals are there in Winterport?

Expedia has 6 vacation rentals for your stay in Winterport.

What can I see and do in Winterport?

While exploring the area, visit family-friendly sights like The Sports Arena, or get outside and enjoy nature at Penobscot River. In the larger area, you’ll find Winterport Winery and Penobscot Narrows Bridge and Observatory.

What are vacation rentals like in Winterport?

Vacation rentals are privately owned properties you can book for several days or longer in Winterport. Vacation rentals offer extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family gatherings.