Windham holiday lettings

We found 635 holiday rentals — enter your dates for availability

Discover a selection of 10 homes and other holiday rentals in Windham that are perfect for your trip. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Windham

Showing deals for:6 Mar - 13 Mar

Image gallery for Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Fully stocked kitchen with plenty of room to prepare a family dinner
10 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chester, VT

7% off
Price is £3,100
for 7 nights, 1 chalet
£443 per night
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

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Choose a holiday rental for your Windham getaway

Learn about the unique charm of Windham with a stay in a holiday home rental. This city has something for everyone. Stratton Mountain Resort and Mount Snow are just a couple of the must-see attractions in the area. 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.

Activities and attractions in and around Windham

Are you hoping to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Windham a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Stratton Mountain Resort (10.6 mi / 17.1 km)
  • Mount Snow (17.8 mi / 28.6 km)
  • Magic Mountain Ski Resort (2.6 mi / 4.2 km)
  • Jamaica State Park (4.7 mi / 7.6 km)
  • Viking Nordic Center (4.7 mi / 7.6 km)
  • Stratton Mountain Golf Course (5 mi / 8 km)

Exploring the natural landscape of Windham

Whether you're an adventurous traveller or just want to appreciate the scenery, Windham is a great place to spend some time outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Lowell Lake State Park (4 mi / 6.5 km)
  • Emerald Lake State Park (16 mi / 25.8 km)
  • Battenkill River (16.4 mi / 26.5 km)
  • Green Mountain National Forest (16.9 mi / 27.2 km)
  • Buttermilk Falls (18.2 mi / 29.2 km)
  • Winhall River (6.2 mi / 10 km)

Transport to and around Windham

The nearest airport is in Springfield, VT (VSF-Hartness State), located 15.5 mi (24.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 26.9 mi (43.3 km) away.

Frequently asked questions

What is the best area to stay in Windham when booking a holiday rental?
When considering a holiday rental in Windham, Vermont, a popular area to stay is the charming neighbourhood surrounding the Windham Mountain Resort. This area not only offers easy access to the slopes for skiing and snowboarding in winter but also provides a plethora of outdoor activities during the warmer months, such as hiking and mountain biking. The resort is a major draw for visitors, making it a lively spot with numerous rental properties available, ensuring you'll find something that suits your preferences.

Another delightful option is the village centre, which is characterised by its quaint shops and local eateries. Here, you can immerse yourself in the local culture while enjoying the picturesque scenery. The nearby Williams River is superb for those who enjoy fishing or simply want to take a peaceful walk along its banks. With a variety of holiday rentals available, this area offers a blend of convenience and charm, making it an ideal base for exploring the beauty of Windham and its surrounding attractions.
How much does it cost to rent a holiday home in Windham?
Prices for holiday rentals in Windham 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 Windham 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 Windham holiday house rentals?
You can find great discounts on house rentals in Windham 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 Windham?
A long-stay holiday rental in Windham 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 Windham holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Windham 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 Windham for a holiday rental?
March is the most popular time to visit Windham, Vermont, as it marks the tail end of the winter season, providing ample opportunities for skiing and snowboarding enthusiasts to enjoy the fresh powder on the slopes. The crisp, cool temperatures, typically ranging from -5 to 5 degrees Celsius, create an ideal setting for outdoor activities, making it a great escape for those seeking adventure amidst picturesque snowy landscapes.

As the peak tourist season runs from July to September, visitors flock to Windham for its vibrant summer activities, including hiking, mountain biking, and exploring the local craft fairs. The warm summer months offer a bustling atmosphere filled with fellow travellers, allowing you to soak in the lively community spirit and partake in numerous outdoor festivals.

For those looking to enjoy a more tranquil experience while also saving on costs, consider planning your visit in December. This month presents a magical winter wonderland, great for cosy getaways and enjoying the festive spirit, all while avoiding the crowds.
How early should I book a Windham holiday rental?
Book your Windham 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.
What are the top attractions in Windham?
In Windham, Vermont, visitors can explore a variety of attractions that showcase the area's natural beauty and outdoor activities. The nearby Stratton Mountain Resort offers skiing and snowboarding in winter, along with hiking and mountain biking trails during the warmer months. This resort is a popular draw for those seeking both adventure and relaxation.

The quaint village of Jamaica is not far and presents charming shops, local eateries, and access to the scenic Jamaica State Park, which features beautiful walking trails and picnic areas along the West River.

For those interested in a more relaxed pace, the Windham County area is dotted with picturesque landscapes and opportunities for leaf-peeping in the fall. The nearby Green Mountain National Forest also provides ample opportunities for hiking and wildlife observation, making it a great spot for nature enthusiasts.
Can I change or cancel my Windham home rental booking on Vrbo?
To find Windham 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 Windham 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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