Winslow holiday lettings

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August 2025

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Discover a selection of holiday rentals in Winslow that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winslow

Showing deals for:14 Nov - 21 Nov

Relax by the water at Sunset Chalet. With a canoe ready for adventure and a chair just waiting for you, enjoy the perfect spot to unwind and take in the serene views of the lake and surrounding nature.

Exceptional

(25 reviews)

Sunset Chalet Lakefront Hot Tub Game Room

Belgrade, ME

8% off

£457 per night

includes taxes & fees

Exceptional

(43 reviews)

Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks

Belgrade, ME

8% off

£200 per night

includes taxes & fees

Exceptional

(15 reviews)

BELGRADE LAKES MAINE GREAT POND PRIVATE 2-BEDROOM COTTAGE 15 FEET FROM WATER

Belgrade, ME

8% off

£191 per night

includes taxes & fees

Exceptional

(25 reviews)

Sunny, spacious and updated lake cottage - amazing views & steps from the water!

Oakland, ME

8% off

£614 per night

includes taxes & fees

Exceptional

(11 reviews)

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

Oakland, ME

15% off

£205 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Winslow

The Modern Maine Retreat

Sleeps 9 · 4 bedrooms · 3 bathrooms

Charming Cabin on forty acres of beautiful fields located in Mid-Coast Maine

Sleeps 4 · 1 bedroom · 1 bathroom

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Sleeps 6 · 2 bedrooms · 1+ bathroom

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 out more about Winslow

Delight in the riverfront landscape of Winslow

Enjoy the history and other features of Winslow. This scenic city attracts visitors thanks to its riverfront and bird watching. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Winslow

Are you hoping to find top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Winslow has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

Belgrade Lakes Golf (13 mi / 20.9 km)
Natanis Golf Course (9.3 mi / 14.9 km)
Eaton Mountain (15.2 mi / 24.5 km)
Quarry Road Trails (3.1 mi / 4.9 km)
Tree Spirits (4.1 mi / 6.6 km)
Samantha Smith (17.7 mi / 28.5 km)

Exploring the natural features in Winslow

Whether you're an adventurous traveller or just want to take in the scenery, Winslow is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

Kennebec River (0.4 mi / 0.7 km)
Belgrade Lakes Chain (10.8 mi / 17.4 km)
Sandy Pond (15.7 mi / 25.2 km)
St George Lake (18 mi / 29 km)
Lovejoy Pond (7.7 mi / 12.4 km)
Kennebec River Rail Trail (17.9 mi / 28.8 km)

Travelling to and around Winslow

Fly into Waterville, ME (WVL-Robert Lafleur), the closest airport, located 3 mi (4.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Augusta, ME (AUG-Augusta State), which is 17.9 mi (28.8 km) away.

Frequently asked questions

What is the best area to stay in Winslow when booking a holiday rental?

When considering a holiday rental in Winslow, Maine, the area around the picturesque Kennebec River is an excellent choice. This neighbourhood offers a delightful blend of natural beauty and accessibility to local attractions. Staying here provides easy access to the scenic Riverwalk, which is superb for leisurely strolls or cycling while enjoying the serene views of the water.

Additionally, the Winslow town centre is nearby, where you can explore charming local shops and cafes, creating a vibrant atmosphere for both relaxation and socialising. The area is also close to the historic Fort Halifax Park, which is a wonderful spot for picnics and offers insights into the region's history.

How much does it cost to rent a holiday home in Winslow?

Prices for holiday rentals in Winslow 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 Winslow 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 Winslow holiday house rentals?

You can find great discounts on house rentals in Winslow 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.

Can I find long-stay holiday rentals in Winslow?

A long-stay holiday rental in Winslow 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 any Winslow holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Winslow 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.

How early should I book a Winslow holiday rental?

Book your Winslow 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 Winslow home rental booking on Vrbo?

To find Winslow 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 Winslow 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.