Photo by Linda Kloss

Winterport holiday rentals

We found 249 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Winterport that are 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:20 Nov - 27 Nov

Exterior
Dining
Living area
Private kitchen
Exceptional
(7 reviews)

Welcome to The Wonky Donkey! Where life can relax with a little humor & sanity

Stockton Springs

7% off
AU$3,733
for 7 nights, 1 home
AU$533 per night
includes taxes & fees
Welcome to The Wonky Donkey! Where life can relax with a little humor & sanity
the deck on the backside of the cabin, facing the cove and tidal water
Property grounds
Dining
Room
Exceptional
(44 reviews)

On Mill Cove. Close to Acadia, restaurants, kayaking, hiking trails..

Stockton Springs

8% off
AU$3,264
for 7 nights, 1 cabin
AU$466 per night
includes taxes & fees
On Mill Cove. Close to Acadia, restaurants, kayaking, hiking trails..
Living area
Living area
Private kitchen
Exterior detail
Exceptional
(10 reviews)

Comfort, Style, and Convenience

Bangor

8% off
AU$2,390
for 7 nights, 1 home
AU$341 per night
includes taxes & fees
Comfort, Style, and Convenience
Terrace/patio
Interior
Exterior detail
Interior
Exceptional
(38 reviews)

Classic Log Home on Pristine Maine Pond<br>Kayaking Heaven, Loons, Bald Eagles<br>

Bucksport

12% off
AU$2,422
for 7 nights, 1 home
AU$346 per night
includes taxes & fees
Classic Log Home on Pristine Maine Pond<br>Kayaking Heaven, Loons, Bald Eagles<br>
Private kitchen
Interior
Custom made spiral staircase to access the new basement game room & bar
Property grounds
Exceptional
(27 reviews)

Sunrise Views Cabin with AC, Game Room & Bar

Hampden

8% off
AU$2,774
for 7 nights, 1 cabin
AU$396 per night
includes taxes & fees
Sunrise Views Cabin with AC, Game Room & Bar
Interior
Property grounds
Living area
Dining
Exceptional
(41 reviews)

Maine Wilderness Oasis: Swimming, Hiking, Fishing, Boating

Bucksport

8% off
AU$3,734
for 7 nights, 1 home
AU$533 per night
includes taxes & fees
Maine Wilderness Oasis: Swimming, Hiking, Fishing, Boating

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Winterport Winery (0.4 mi / 0.6 km)
  • Bucksport Golf Club (5.9 mi / 9.5 km)
  • Penobscot Valley Country Club (17.5 mi / 28.1 km)
  • Maine Forest and Logging Museum (19.3 mi / 31 km)
  • Bangor Municipal Golf Course (10.9 mi / 17.6 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)
  • Phillips Lake (12.5 mi / 20.1 km)
  • Branch Lake (14 mi / 22.6 km)
  • Toddy Pond (15.4 mi / 24.8 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, the best area to stay is near the picturesque waterfront. This charming neighbourhood offers a delightful blend of scenic views and convenient access to local attractions. You'll find a variety of properties here, ranging from cosy cottages to spacious family homes, all within close proximity to the serene Penobscot River.One of the top attractions in this area is the Winterport Winery, known for its unique fruit wines and beautiful vineyard setting, making it a great spot for a leisurely afternoon. Additionally, the nearby Fort Knox State Historic Site is a must-visit, where you can explore the impressive 19th-century fort and enjoy stunning views of the river and surrounding landscape.Staying near the waterfront not only allows you to enjoy these local attractions but also provides a tranquil atmosphere, ideal for a relaxing getaway.
Where are the best areas for renting a beach house in Winterport?
For renting a beach house in Winterport, consider the picturesque shores along the Penobscot River. The area near the Winterport waterfront offers charming holiday rentals with easy access to scenic river views and tranquil sandy spots for relaxing. Many properties in this vicinity come equipped with amenities such as private decks, outdoor seating areas, and fully equipped kitchens, making them ideal for families or groups who want to enjoy a riverside retreat.Further along the river, you might find additional options in the nearby town of Hampden, which boasts riverfront homes that often feature spacious yards, fire pits, and direct access to the water for swimming or kayaking. This area has a community feel, with local shops and eateries nearby, adding convenience for visitors.Additionally, the surrounding countryside provides opportunities for outdoor activities such as hiking and exploring nature trails. Many rentals in the Winterport area come with amenities like barbecues and picnic areas, making them suitable for enjoying warm summer evenings under the stars.
Where are the best Winterport ski resort rentals?
For renting near ski resorts in Winterport, Maine, travellers should consider the nearby area of Camden, which is about a 30-minute drive from the ski slopes at Camden Snow Bowl. This picturesque town offers a selection of cosy cabins and chalets, ideal for families and groups. Many properties feature amenities like wood-burning stoves, fully equipped kitchens, and outdoor decks with scenic views, superb for relaxing after a day on the slopes.In addition to Camden, the surrounding areas like Lincolnville and Rockport also provide charming options. Rentals here often come with access to local attractions, including beaches and hiking trails, and some properties even offer hot tubs or fire pits for evening gatherings. The proximity to local shops and restaurants enhances the convenience for visitors, making it easy to stock up on supplies or enjoy a meal out.Moreover, the area boasts beautiful winter landscapes, making it superb for snowshoeing and cross-country skiing as well.
What is the most popular type of holiday rental accomodation in Winterport?
In Winterport, holiday houses are the most popular type of holiday rental, with around 21 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy the scenic surroundings. Additionally, there are several mobile homes, apartments, and cabins available, offering a range of options for different preferences.
Are there any family house rentals in Winterport?
In Winterport, Maine, there are several family-friendly house rentals available, making it an ideal spot for a family getaway. This charming town offers a mix of cozy homes located among scenic landscapes, providing ample space for relaxation and play. Many of these properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces suitable for children to explore.Visitors can enjoy nearby attractions, such as the serene banks of the Penobscot River, which present opportunities for fishing or leisurely walks. Additionally, the local community is known for its welcoming atmosphere, making it easy for families to feel at home.
Can I rent a holiday home with a pool or hot tub in Winterport?
In Winterport, Maine, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing option for those seeking relaxation during their stay. This quaint town, located along the Penobscot River, offers a variety of properties that cater to different group sizes and preferences. Many rentals come with amenities such as private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, allowing guests to enjoy their time both indoors and outdoors comfortably.The surrounding area also provides opportunities for outdoor activities, including hiking and exploring the picturesque riverfront scenery.
Are there pet-friendly house rentals in Winterport?
In Winterport, there are several pet-friendly house rentals available, making it a suitable destination for travellers with furry companions. Many of these holiday homes come equipped with essential amenities such as fully equipped kitchens, comfortable living spaces, and outdoor areas where pets can enjoy the fresh air.The town is located along the Penobscot River, providing a scenic backdrop for your stay. Nearby, you'll find the picturesque Fort Knox State Historic Site, which offers pleasant walking paths and opportunities for exploration. Additionally, the surrounding area features various parks and trails that are superb for leisurely strolls with your pets, ensuring you have plenty of options for outdoor activities during your visit.
Are there any remote work holiday rentals in Winterport?
In Winterport, Maine, there are approximately 21 remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties come equipped with amenities specifically designed for remote work, including bookable desks and reliable Wi-Fi, ensuring a productive environment.Travellers can expect a range of options, from cosy cottages to spacious homes, typically featuring comfortable living areas and well-equipped kitchens for convenient meal preparation. The picturesque town offers a tranquil setting, great for unwinding after a day of work, with local parks and scenic views to explore.Additionally, the nearby Penobscot River provides opportunities for outdoor activities, adding a refreshing touch to your remote work experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winterport?
In Winterport, popular rental amenities include kitchens, which allow guests to prepare their own meals and enjoy home-cooked dining. Onsite parking is commonly available, making it convenient for those travelling by car. Many rentals also permit pets, welcoming visitors who wish to bring their furry friends along. Additionally, service animals are accommodated. To enhance the stay, most properties come equipped with coffee and tea makers, superb for enjoying a warm beverage at any time of the day.
When is the best time to visit Winterport for a holiday rental?
The best time to visit Winterport for a holiday rental is during the peak season from December to February, with January being particularly popular. This winter wonderland invites travellers seeking adventure in the snow, with opportunities for activities like snowshoeing, cross-country skiing, and enjoying the picturesque landscape blanketed in white. The charm of Winterport during this time is truly captivating, with its quaint shops and local eateries offering a warm retreat after a day of outdoor fun.January boasts average temperatures ranging from -6 to 2 degrees Celsius, making it an ideal time for those who relish the crisp winter air and the beauty of a snowy backdrop. The town comes alive with festive decorations, and the community often hosts winter events that add to the holiday spirit.For those who prefer a quieter experience, consider visiting in May. This transitional month offers milder weather as spring unfolds, with temperatures averaging around 10 to 15 degrees Celsius. Visitors can enjoy the blooming countryside, explore scenic hiking trails, and partake in local festivals celebrating the arrival of warmer days.Ultimately, your choice will depend on whether you're eager to embrace the vibrant winter activities in January or prefer the peaceful awakening of spring in May.
What are the top attractions in Winterport?
In Winterport, Maine, visitors can enjoy a variety of attractions that showcase the area's natural beauty and rich history. The Penobscot River is a focal point, offering opportunities for kayaking and fishing, with scenic views that can be appreciated from various points along the riverbank.The historic district features charming architecture and sites like the Winterport Union Meeting House, which reflects the town's heritage. Nearby, the Winterport Winery offers tastings and tours, allowing guests to sample local wines in a picturesque setting.For outdoor enthusiasts, the surrounding countryside provides ample hiking and biking trails, particularly in the nearby parks that feature lush landscapes and wildlife viewing opportunities.
Are all fees included in the Winterport holiday homes prices shown on Stayz?
Stayz 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.
Are there any Winterport holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Winterport holiday homes?
You can find great discounts on holiday homes in Winterport on Stayz, 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.
Can I change or cancel my Winterport holiday home booking on Stayz?
To find Winterport holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winterport?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winterport holiday home?
Book your Winterport holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winterport?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winterport to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.