Photo by Linda Kloss

Winterport Holiday 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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Winterport

1812 Pierce House

3.5 star property
1812 Pierce House

Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill

10.0 out of 10, Exceptional, (3)
"Older home with charm and some nice updates. It was perfect for our family of 6 and our dog. Kids appreciated the private pool on the 95° days and the dog loved the river. Couch is super comfortable and the outside area let us spend time together. Acadia is just over an hour away and it was a great home away from home for us."
Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill

NEW 2025 RV, 1 Bedroom WiFi AC in Serene Winterport with Coast and Bangor nearby

NEW 2025 RV, 1 Bedroom WiFi AC in Serene Winterport with Coast and Bangor nearby

Peaceful Bangor Getaway | Clean & Cozy 2BR Home

2.0 star property
9.8 out of 10, Exceptional, (9)
"cozy stay, close to everything Bangor! "
Peaceful Bangor Getaway | Clean & Cozy 2BR Home

Lake Front on Beech Hill Pond, 2 Kayaks, Canoe, Paddle Board Provided

9.8 out of 10, Exceptional, (61)
"Lovely property! Have a great time relaxing and enjoying nature."
Lake Front on Beech Hill Pond, 2 Kayaks, Canoe, Paddle Board Provided

Country Charm: Cozy getaway in delightful Searsport

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a wonderful stay at this charming property in Searsport! Patty was an excellent host—very responsive and attentive, which made everything smooth and stress-free. The place itself was spotless, cozy, and had everything I needed for a comfortable stay. From the thoughtful touches to the peaceful setting, it truly felt like a home away from home. Highly recommend for anyone looking for a relaxing and well-kept retreat!"
The price is NZ$339
includes taxes & fees
15 July - 16 July
Country Charm: Cozy getaway in delightful Searsport

ISLAND VACATION, Canoe 5 minutes to Island and relax

9.8 out of 10, Exceptional, (28)
"Absolutely loved our stay here. Fantastic location and great hosts. Would love to return."
ISLAND VACATION, Canoe 5 minutes to Island and relax

Cozy Cabin By The Pond, Sleeps 2

10.0 out of 10, Exceptional, (172)
"Extremely cozy, easy to find, great hosts, close to some very cute towns."
The price is NZ$333
includes taxes & fees
13 July - 14 July
Cozy Cabin By The Pond, Sleeps 2

Bucksport Bliss A Luxe Log Cabin. Waterview & Private.

2.0 star property
10.0 out of 10, Exceptional, (7)
"The property was clean, well stocked and very comfortable. The neighborhood was quiet, yet close enough to Brewer and Bucksport to shop. We had a wonderful time. Justin was amazing answering questions promptly and was able to help both before and during our visit."
Bucksport Bliss A Luxe Log Cabin. Waterview & Private.

MaineStay Cottage #5 With Fireplace & Fully Stocked Kitchen in Hampden/Bangor

10.0 out of 10, Exceptional, (46)
"Private, Homey and very comfortable!!"
The price is NZ$361
includes taxes & fees
21 July - 22 July
MaineStay Cottage #5 With Fireplace & Fully Stocked Kitchen in Hampden/Bangor

near Acadia, Bar Harbor and Booth Bay

9.8 out of 10, Exceptional, (108)
"All that it was hoped to be. It was clean and very inviting, not very many places look like the photos this place did it met all expectations great place"
near Acadia, Bar Harbor and Booth Bay

Rustic farmstay in a barn studio apartment

2.0 star property
10.0 out of 10, Exceptional, (2)
"Adorable loft studio- the ideal hideaway for a quick recharge and reset.Sweet,accomodating hosts and comfy, rustic digs. Perfection!"
The price is NZ$208
includes taxes & fees
16 July - 17 July
Rustic farmstay in a barn studio apartment

Charming Lake front Cottage w/dock close to Acadia National Park & Bar Harbor

9.4 out of 10, Exceptional, (46)
"We used the cabin as a home base to explore Acadia while having a fun and beautiful place to come back and see the sunsets and sunrises on the water. The little heater was enough to keep us warm during the chilly fall week we were there. Was a great spot for the two of us!"
Charming Lake front Cottage w/dock close to Acadia National Park & Bar Harbor

Quiet guest cottage-private setting! Hiking, boating, swimming, wildlife near.

10.0 out of 10, Exceptional, (6)
"Awesome place, nice to come back from the bustle of Acadia and Bar Harbor to this quiet sanctuary, Host;s were great!"
Quiet guest cottage-private setting! Hiking, boating, swimming, wildlife near.

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!

Cozy home in Bangor Maine

9.4 out of 10, Exceptional, (18)
"Comfortable stay. Lots of room. Great parking. "
The price is NZ$545
includes taxes & fees
21 July - 22 July
Cozy home in Bangor Maine

Modern, Dogs Welcome, Near Acadia National Park & Bar Harbor

10.0 out of 10, Exceptional, (153)
"Great property. Wonderful trip. "
Modern, Dogs Welcome, Near Acadia National Park & Bar Harbor

Beautiful lake side cottage

9.4 out of 10, Exceptional, (29)
"Very clean cute property on the waterfront! Enjoyed our stay and would love to return again!"
Beautiful lake side cottage

Blue Cabin by the Brook in Surry close to Acadia National Park and Bar Harbor

10.0 out of 10, Exceptional, (1)
"The property in Surry was just perfect for our use. The property is one of 3 manufactured homes on this property. The rental was clean, comfortable and perfect for the two of us. It is located on a quiet road and very drivable to many sightseeing attractions in the immediate area, Acadia NP being one of them. The AC came in handy during our stay as the weather was warm. The basic kitchen was good for us as we ate out every night. The washer and dryer were a good perk also. Overall a very good...
Blue Cabin by the Brook in Surry close to Acadia National Park and Bar Harbor

Waterfront cottage with deep water dock, ocean front.

9.8 out of 10, Exceptional, (96)
"The host made the check in process very easy. The cottage was clean and prepared for us when we got there. It was a perfect getaway weekend! "
Waterfront cottage with deep water dock, ocean front.
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

Frequently asked questions

Are there holiday rentals in Winterport?

Yes, there are holiday rentals close to the most popular sights in Winterport, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Winterport has to offer?

1812 Pierce House: This highly rated holiday home rental in Winterport is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop. Another good choice for your trip to Winterport is Serene Waterfront Home with In-Ground Pool, River Views, Spacious Deck, & Grill.

How many holiday rentals are there in Winterport?

Expedia has 6 holiday rentals for your stay in Winterport.

What can I see and do in Winterport?

While exploring the area, visit family-friendly sights like Maine Discovery Museum, or get outside and enjoy nature at Penobscot River. In the wider area, you’ll find Winterport Winery and Penobscot Narrows Bridge and Observatory.

What are holiday rentals like in Winterport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winterport. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.