Photo by Linda Kloss

Winterport holiday lettings

We found 250 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Winterport to find one that's perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, such as parking and a fireplace. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winterport

Showing deals for:30 Jan - 6 Feb

Image gallery for 1790 Historic home on the Narramissic River in Orland Village

Exterior
9.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

1790 Historic home on the Narramissic River in Orland Village

Orland, ME

7% off
Price is £7,061
for 7 nights, 1 home
£1,009 per night
includes taxes & fees
1790 Historic home on the Narramissic River in Orland Village

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Find the perfect holiday rental for your Winterport getaway

Enjoy the wineries and other features of Winterport. This city is well-known for its shopping and restaurants. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Winterport

Are you looking for attractions to visit while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Winterport a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Hermon Mountain (11.3 mi / 18.2 km)
  • Perry's Nut House (15.7 mi / 25.3 km)
  • Winterport Winery (0.4 mi / 0.6 km)
  • Bucksport Golf Club (5.9 mi / 9.5 km)
  • Bangor Municipal Golf Course (10.9 mi / 17.6 km)
  • Playland Adventures (11.1 mi / 17.8 km)

Exploring the natural features in Winterport

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Winterport is a great place to spend some time outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Swan Lake (9.4 mi / 15.2 km)
  • Waterfront Park (11.5 mi / 18.5 km)
  • Penobscot River (11.6 mi / 18.7 km)
  • Branch Lake (14 mi / 22.6 km)
  • Belfast City Park (17 mi / 27.4 km)
  • Green Lake (18 mi / 29 km)

Transport to and around Winterport

The nearest airport is in Bangor, ME (BGR-Bangor Intl.), located 11.9 mi (19.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Bar Harbor, ME (BHB-Hancock County - Bar Harbor), which is 27.3 mi (43.9 km) away.

Frequently asked questions

What is the best area to stay in Winterport when booking a holiday rental?
When considering a holiday rental in Winterport, Maine, a popular area to stay is near the charming downtown district. This area not only offers a quaint, small-town atmosphere but also provides easy access to local attractions and points of interest. One of the highlights nearby is the Winterport Winery, where visitors can enjoy tastings and tours of this lovely establishment that showcases the area's unique wine production. Additionally, the scenic Penobscot River is just a stone's throw away, offering opportunities for leisurely strolls and picnics along its banks.
How much does it cost to rent a holiday home in Winterport?
Prices for holiday rentals in Winterport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winterport to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winterport holiday house rentals?
You can find great discounts on house rentals in Winterport on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Winterport?
For renting a beach house in Winterport, Maine, travellers should consider the scenic areas along the Penobscot River and the nearby coastal regions. The waterfront properties along the river offer beautiful views and easy access to water activities such as kayaking and fishing. Many of these rentals come equipped with amenities like private docks, outdoor seating areas, and spacious kitchens suitable for family gatherings.

In addition, the nearby town of Belfast, located a short drive away, features charming beach homes with stunning views of Penobscot Bay. These properties often include features like decks for enjoying sunsets, access to sandy beaches, and modern conveniences such as Wi-Fi and air conditioning. The town itself is known for its vibrant arts scene and delightful local shops and restaurants, adding to the appeal of a beach rental in the area.
What is the most popular type of holiday rental accomodation in Winterport?
In Winterport, holiday houses are the most popular rental option, with several available throughout the area. These properties typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many also feature outdoor spaces such as gardens or patios, superb for enjoying the scenic beauty of Maine. Cottages are another common choice, providing a quaint, rustic charm with amenities like fireplaces and porches for relaxation. Additionally, there are several condos and mobile homes that cater to those looking for more compact accommodations, often equipped with modern conveniences.
Are there any family house rentals in Winterport?
In Winterport, Maine, there are ten family-friendly house rentals available, making it a suitable destination for those travelling with children. The town offers a charming atmosphere with a range of properties that typically include spacious living areas and fully equipped kitchens, allowing families to prepare their meals comfortably. Many homes feature outdoor spaces where children can play and explore, along with amenities such as Wi-Fi and laundry facilities for added convenience.
Can I rent a holiday home with a pool or hot tub in Winterport?
In Winterport, there are several holiday homes available for rent that feature pools and hot tubs, providing a wonderful option for travellers looking to enjoy some relaxation and leisure during their stay. The charming town, located along the Penobscot River, offers a variety of properties that may include amenities such as private swimming pools, hot tubs, and spacious outdoor areas for entertaining. Many rentals also come equipped with fully stocked kitchens and comfortable living spaces, ensuring a pleasant family getaway.
Can I find long-stay holiday rentals in Winterport?
A long-stay holiday rental in Winterport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winterport?
In Winterport, there are several pet-friendly house rentals available, making it an excellent choice for travellers who wish to bring their furry companions along. Many of these properties offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas that cater to families or groups.
Are there any remote work holiday rentals in Winterport?
In Winterport, Maine, there are several holiday rentals suitable for remote work. Many of these properties come equipped with essential amenities such as Wi-Fi, dedicated desks, and comfortable chairs, providing a conducive environment for productivity. Travellers can expect a mix of charming homes and modern apartments, often featuring spacious living areas and well-equipped kitchens, allowing for a comfortable and convenient stay. The region offers a peaceful atmosphere, ideal for those seeking a balance between work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winterport holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winterport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winterport?
In Winterport, holiday rentals typically feature a variety of amenities that enhance the guest experience. Most properties come equipped with a kitchen, allowing travellers to prepare their own meals. Many rentals also include a patio or garden, providing outdoor space for relaxation or social gatherings. Additionally, guests can expect conveniences such as coffee makers in the rooms and essential cookware, dishware, and utensils for dining in.
When is the best time to visit Winterport for a holiday rental?
January is the most popular month to visit Winterport, especially for those seeking a winter wonderland experience. The peak season runs from December to February, when visitors flock to the area for a variety of outdoor activities, such as snowshoeing, cross-country skiing, and enjoying the beautiful snowy landscapes. With temperatures typically hovering around -5 to 0 degrees Celsius, it's a superb time for those who embrace the chill and want to partake in winter sports or simply enjoy the scenic beauty of the snowy surroundings.

For travellers who prefer a quieter atmosphere, May presents an excellent opportunity to explore Winterport without the hustle and bustle of the high season. The spring weather is generally mild, making it comfortable for outdoor activities such as hiking and sightseeing. This transition period offers a chance to witness the region's blooming flora and lively wildlife, all while enjoying the peacefulness of less crowded attractions.
How early should I book a Winterport holiday rental?
Book your Winterport holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winterport home rental booking on Vrbo?
To find Winterport holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winterport holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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