Winslow holiday lettings

We found 157 holiday rentals — enter your dates for availability

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.

Find spaces that suit your style

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

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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)
  • 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)
  • Natanis Golf Course (9.3 mi / 14.9 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)
  • St George Lake (18 mi / 29 km)
  • Capitol Park (18.3 mi / 29.5 km)
  • Lovejoy Pond (7.7 mi / 12.4 km)
  • Sandy Pond (15.7 mi / 25.2 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

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.
When is the best time to visit Winslow for a holiday rental?
The most popular time to visit Winslow is during the peak season from July to September, when the area comes alive with vibrant summer energy. This period is ideal for those looking to enjoy outdoor activities, such as kayaking on the Kennebec River or exploring the beautiful local parks. The warm weather, typically ranging from 15 to 30 degrees Celsius, makes it great for sightseeing and taking leisurely strolls along the charming streets filled with quaint shops and eateries.

July stands out as the prime month for visitors, as it offers the highest number of events and activities, including local festivals that celebrate the region's culture. The lively option draws many travellers, creating a sense of community and excitement.

For those seeking a more budget-friendly option, consider planning your visit in December. While this month is quieter, it brings its own unique charm with festive decorations and a peaceful ambiance, great for relaxing and enjoying the winter scenery.

Ultimately, the best time to visit Winslow depends on your preferences—whether you want to immerse yourself in the bustling summer vibe or enjoy a tranquil winter retreat.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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