Photo by Linda Kloss

Winterport holiday lettings

We found 252 holiday rentals — enter your dates for availability

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July 2025

August 2025

Discover a selection of 6 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:24 Oct - 31 Oct

Exceptional

(6 reviews)

Country Charm: Cozy getaway in delightful Searsport

Searsport, ME

21% off

£104 per night

includes taxes & fees

Exceptional

(5 reviews)

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

Orrington, ME

8% off

£212 per night

includes taxes & fees

Living room with open concept to dining table. TV with Roku. 1st floor

Exceptional

(11 reviews)

2 story cozy home. Walk to downtown Bangor and Brewer. Safe quiet neighborhood

Brewer, ME

8% off

£232 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Winterport

Showing deals for: 22 Oct - 25 Oct

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

Sleeps 8 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

£403 per night

includes taxes & fees

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

Sleeps 30 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

£80 per night

includes taxes & fees

Stunning Remodeled Coastal Oasis - Gorgeous Water Views, A/C, Dogs, Firepit

Sleeps 12 · 4 bedrooms · 3 bathrooms

for 3 nights, 1 cottage

£702 per night

includes taxes & fees

Luxury Cottage on the Penobscot River with Breathtaking Views

2024 Remodel - Magnificent Water View, A/C, Dogs, Yard, Games, Fire Pit, Trendy

Sleeps 6 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 cottage

£353 per night

includes taxes & fees

Luxury Cottage overlooking Penobscot River near Acadia

River Retreat - Stylish, Gorgeous Water View, Dogs, Fire Pit, Secluded, Games

Sleeps 6 · 2 bedrooms · 1 bathroom

for 3 nights, 1 cottage

£353 per night

includes taxes & fees

Top rated rentals - Winterport

Premier Host

The perfect getaway!

Not sure what more you can ask for in a rental - the studio was clean, cozy, and well equipped, the firepit and views over the pond were phenomenal, the location is great, and Sonya is the kindest host who made the whole process so smooth and effortless. Thanks for having us Sonya, we already can’t wait to go back :)

Nina D.

Stayed Sept 2023

Premier Host

Wonderful stay by the lake

We had a lovely peaceful time at this spotlessly clean and cosy rental. Breathtaking views of the lake. Good communication with friendly hosts. Thank you!

Valerie B.

Stayed Oct 2022

The historical Big Red House - the BRH for short. Welcome! 🏠❤️

Premier Host

A beautiful historic home away from home

A gorgeous old house, steeped in history, with so much character. Lovingly looked after, spacious, charming with everything you’d need for a large family staying in Bangor. Great location too, only about 20 minutes walk to downtown Bangor and less than 10 minutes walk to Stephen King’s home (if you’re interested, or a fan) . Cindy was a fabulous host, I couldn’t be more grateful for her phone call when I arrived late and in the dark due to flight delays. She saw me trying to get access on her security camera and wanted to make sure I was okay. I loved my stay in this house, and even though I was by myself (My travelling companion cancelled at the last minute) I would recommend this as a retreat for one, or as a fabulous, spacious place for a family.

Dora B.

Stayed Dec 2021

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, 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)
Bangor Municipal Golf Course (10.9 mi / 17.6 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)
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 most popular type of holiday rental accommodation in Winterport?

Houses are the most popular kind of holiday rental in Winterport, according to our data. Even if you've got something different in mind, Vrbo has holiday homes in many shapes and sizes. Explore our options to find your ideal match.

How much does it cost to rent a holiday rental in Winterport?

Length of stay, season and property type are some of the conditions that can affect the price of a holiday home. Simply enter your dates of travel to find your dream escape. From comfy cabins to plush villas, all Vrbo holiday rentals provide amazing value.

How much does it cost to rent a beach house in Winterport?

The average price for a holiday rental by the beach in Winterport depends on when you're visiting the area and the type and size of property you're searching for. You can quickly and easily find prices on Vrbo by entering your preferred travel dates and destination. Then use our filters to pick the number of bedrooms and amenities important to you, like air conditioning, a pool and WiFi.

Are there pet-friendly holiday rentals in Winterport?

Pack a travel bag and a bone for your pup because Winterport has five properties that throw out the welcome mat to pets. Let your furriest friend join in with the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and dates, then check the "Pets allowed" filter box.

What are popular rental amenities in Winterport?

Some of the most popular rental amenities people search for in Winterport are a swimming pool, a fireplace and a nearby river. Whether you're hitting the road with family, pals or even pets, Vrbo holiday rentals come with the best amenities for making new memories with the people you love.

Are there large group holiday rentals in Winterport?

Take your pick of two Vrbo holiday homes in Winterport that can accommodate a group of five or more people. You'll get all the space and privacy you need to have fun with the people you're holidaying with — and nobody else.

Are there holiday rentals in Winterport that welcome kids?

Gather your whole family for a fun-packed adventure in Winterport at one of our five family-friendly holiday rentals. A lot of these stays come with amenities that are perfect for trips with the little ones, such as full kitchens, living rooms and private pools. Just click on the "Properties good for families" filter box and pick out your favourite.

What are the top attractions for families in Winterport?

There's a ton of amazing things to see and do with the family in Winterport, such as:

Fort Knox State Historic Site
Fort Knox State Park
Silver Lake

Are there one-bedroom holiday rentals in Winterport?

You'll find two one-bedroom properties in Winterport to select from. A one-bedroom holiday home is an excellent choice if it's just two of you or if you're holidaying alone. Toss in more privacy, convenience and space compared to a hotel, and you're bound to have a trip to remember.

Are there holiday rentals with WiFi in Winterport?

Whether you want to keep up with the news, send a few emails or surf social networks, there are two holiday homes with WiFi in Winterport. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.

How can I find holiday rentals with air conditioning in Winterport?

Pick from three holiday homes with air conditioning in Winterport giving you that gentle, cool breeze and extra bit of comfort. Just enter your desired travel dates and then make use of our filter tool to help you locate stays with air conditioning.

How old do you have to be to rent a holiday rental in Winterport?

It's a good idea to check with the Winterport holiday rental you want on Vrbo as age restrictions differ. However, generally it's 16, 18 or 21.

How long can I rent a holiday rental in Winterport for?

The amount of time you can stay in a Winterport holiday home for depends on each property. Just put in your travel dates to find available options offering extended stays. They include all the things you need to make your extended getaway more enjoyable and convenient, such as kitchens and air conditioning. Some Vrbo holiday rentals may also offer weekly or monthly discounts, so you can stick around for longer for less.