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Winterport Holiday Rentals

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Holiday Rentals in Winterport

Our top choices for Winterport holiday rentals

1812 Pierce House

3.5 star property
1812 Pierce House

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

10.0 out of 10, Exceptional, (1)
"Great place to stay"
NEW 2025 RV, 1 Bedroom WiFi AC in Serene Winterport with Coast and Bangor nearby

Cozy 2 BR by River- Crooked Steeple Hall

4.0 star property
Cozy 2 BR by River- Crooked Steeple Hall

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

Charming studio in Bangor Maine on Broadway park.

9.4 out of 10, Exceptional, (9)
"Gary is great, easy walk or uber to downtown or the Amphitheatre. Very nice comfortable spot. "
The price is AU$224
includes taxes & fees
22 Sept - 23 Sept
Charming studio in Bangor Maine on Broadway park.

The Yellow 2 Bedroom Cottage @Twin Hills Cottages

8.8 out of 10, Excellent, (20)
"This cottage perfectly met our needs for a clean and comfortable place to stay the night."
The price is AU$340
includes taxes & fees
15 Sept - 16 Sept
The Yellow 2 Bedroom Cottage @Twin Hills Cottages

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

9.8 out of 10, Exceptional, (68)
"Peaceful setting to relax and enjoy Maine. The home was perfectly equipped for a large dinner of Surf and Turf! We would definitely stay at this home again!"
Lake Front on Beech Hill Pond, 2 Kayaks, Canoe, Paddle Board Provided

Quiet single-level fully furnished house

10.0 out of 10, Exceptional, (36)
"Great location, Great Host and great Accommodations!"
The price is AU$355
includes taxes & fees
23 Sept - 24 Sept
Quiet single-level fully furnished house

Peaceful Bangor Getaway | Clean & Cozy 2BR Home

2.0 star property
10.0 out of 10, Exceptional, (12)
"Place was clean and host was very communicative"
Peaceful Bangor Getaway | Clean & Cozy 2BR Home

The Blue Cottage@ Twin Hills Cottages

9.2 out of 10, Wonderful, (14)
"Great location with easy access to the local town. "
The price is AU$322
includes taxes & fees
23 Sept - 24 Sept
The Blue Cottage@ Twin Hills Cottages

Clean Cozy Waterfront Cottage - Perfect for Family Relaxation and Recreation

10.0 out of 10, Exceptional, (3)
"Wonderful cabin very private and quiet. Had everything we needed. Ralph the host was very helpful and quick to reply to any questions we may have had. Will definitely be back. "
Clean Cozy Waterfront Cottage - Perfect for Family Relaxation and Recreation

Adorable private cottage with lake views and access.

10.0 out of 10, Exceptional, (60)
"Beautiful property! It was well maintained and very clean. Wonderful antiques and tastefully decorated. It was very warm outside and the only negative was no air conditioning on the main level making it impossible to stay there during the day."
Adorable private cottage with lake views and access.

spacious clean vacation unit near Bangor and on your way to Acadia National Park

9.2 out of 10, Wonderful, (27)
"This space was cean and spacious. It was conveniently located to Bangor and the host was very easy to communicate with. I would stay there again."
The price is AU$455
includes taxes & fees
15 Sept - 16 Sept
spacious clean vacation unit near Bangor and on your way to Acadia National Park

Tranquil Lakefront Cottage Near Acadia Nat’l Park.

9.6 out of 10, Exceptional, (107)
"What a wonderful view, loved our stay!"
Tranquil Lakefront Cottage Near Acadia Nat’l Park.

New listing. Charming 3-bedroom lake house in Orrington WiFi, Hot tub, and Sauna

10.0 out of 10, Exceptional, (6)
"Perfect location for seeing all the sites from Bangor to Bar Harbor. "
New listing. Charming 3-bedroom lake house in Orrington WiFi, Hot tub, and Sauna

WATERFRONT Maine Historical Cottage with Separate Guest Cottage

8.6 out of 10, Excellent, (8)
"loved staying here, such a charming spot. "
WATERFRONT Maine Historical Cottage with Separate Guest Cottage

Charming 3 bedroom on Beech Hill Pond close to Ellsworth and Bar Harbor WiFi, AC

10.0 out of 10, Exceptional, (30)
"The house was very nice and clean. "
Charming 3 bedroom on Beech Hill Pond close to Ellsworth and Bar Harbor WiFi, AC

Waterfront cottage with deep water dock, ocean front.

9.8 out of 10, Exceptional, (100)
"Beautiful swing and convenient to town. Live the stay even though the weather was less than cooperative."
Waterfront cottage with deep water dock, ocean front.

The James House on Chemo Pond Dogs Welcome

10.0 out of 10, Exceptional, (136)
"It was a great place, very clean and met all of the families needs and the lake setting was awesome. "
The James House on Chemo Pond Dogs Welcome

Mountains Edge Suite -Scenic Bald Mtn.- Your MAINE Adventure Begins Here!

9.8 out of 10, Exceptional, (38)
"Comfortable and relaxing stay for our family for 1 night. Very clean unit with a nice bathroom and kitchen."
The price is AU$423
includes taxes & fees
15 Sept - 16 Sept
Mountains Edge Suite -Scenic Bald Mtn.- Your MAINE Adventure Begins Here!
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.
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Top Winterport Hotel Reviews

Find out more about Winterport

Find out more about Winterport

Everything you need to know about Winterport holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winterport holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winterport holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winterport holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winterport. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winterport holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winterport holiday rentals we have selected for you start as low as AU$224 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winterport rentals

At Expedia, we put the best Winterport holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winterport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winterport holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winterport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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. Our travellers also rate Cozy 2 BR by River- Crooked Steeple Hall as a favourite home for rent in Winterport.

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 The Sports Arena, 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.