Book Windham County holiday rental accommodation: short-term rental properties & homes

Select from 657 houses, 85 apartments and other holiday rentals to find the perfect place for your stay in Windham County. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll have the best amenities for spending time at your home away from home, such as parking and air conditioning. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Popular Windham County destinations on Stayz

Find spaces that suit your style

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Find the best place to stay - Windham County

Quiet country cottage

Sleeps 5 · 2 bedrooms · 2 bathrooms

An exquisite 10 bedroom estate with tons of great amenities. Perfect location!

Most Luxurious 7000 Sq. ft. Log Estate — Pool, Hot Tub, Privacy & Lake Access!

Sleeps 8 · 4 bedrooms · 7+ bathrooms

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Partridge Run Ski House Hot Tub! Booking Sum/Fall/Winter Special Rates Available

Sleeps 25 · 6 bedrooms · 5+ bathrooms

Top rated rentals - Windham County

Absolute gem!

The captivating area of Windham County awaits your stay

The area's entertainment and monuments are just some of the reasons to come on holiday to Windham County. Renowned for its skiing, shopping and snowboarding, this city welcomes all visitors. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Windham County

Are you hoping to find top things to see and do during your stay? Travellers enjoy Windham County for its skiing, snowboarding and hiking. Venture out of your cosy holiday rental and experience everything that Windham County has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Brattleboro Country Club (8.6 mi / 13.9 km)
Mount Snow Golf Course (11.2 mi / 18 km)
The Hermitage Golf Club (13.2 mi / 21.2 km)
The Hermitage Club (13.3 mi / 21.4 km)
Mount Snow (13.5 mi / 21.7 km)
Jamaica State Park (13.6 mi / 21.8 km)

Exploring the mountains and other natural features in Windham County

Whether you're an adventurous traveller or just want to appreciate the scenery, Windham County is a great place to get out in nature. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

Brattleboro Common (10.1 mi / 16.3 km)
Madame Sherris Castle Ruins (10.8 mi / 17.4 km)
Madame Sherri Forest (10.9 mi / 17.5 km)
Hogback Mountain Conservation Area (11.1 mi / 17.9 km)
Lake Raponda (11.2 mi / 18.1 km)
Spofford Lake (11.9 mi / 19.1 km)

Transport options to and around Windham County

If you'd rather travel by train, make your way to Brattleboro Station or Bellows Falls Station to see more of the city.

Frequently asked questions

What is the best area to stay in Windham County when booking a holiday home?

One of the more in-demand areas to book your holiday home in Windham County is Wilmington. Spend your getaway here and experience its must-see attractions, such as The Hermitage Golf Club and Molly Stark State Park.

What is the most popular type of holiday home accommodation in Windham County?

The most desirable types of holiday homes in Windham County are houses. Looking for something different? Stayz has plenty of options to match the needs of our guests, so you’ll see holiday homes in loads of shapes and sizes. The perfect fit is ready and waiting for you — snap up yours today.

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

The average price for a holiday home in Windham County is based on a number of factors, like property type, season and length of stay. Whether you’re searching for a sprawling villa with room to move around or a quaint cottage for just you and your sweetheart, just enter your dates of travel to find stays with exceptional value.

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

The average price for a holiday home close to the beach in Windham County depends on when you’re visiting the area and the type and size of property you want. Find prices easily on Stayz by entering your destination and travel dates. Then make use of the filter tool to select the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a hot tub.

What are popular home amenities in Windham County?

The most popular home amenities people look for in Windham County are a fridge, a microwave oven and an oven. Whether you’re taking a trip with family, pals or even pets, Stayz holiday homes feature the best amenities for fun and relaxation with the people you love.

Are there large group holiday homes in Windham County?

With 326 holiday homes that can sleep 10 guests or more in Windham County, there’s no need to leave anyone off your guest list. From family holidays to special events like birthday and Christmas parties, Stayz will help you find a large group home that fits the occasion.

What are the top attractions for families in Windham County?

Keep the kids busy at these leading family-friendly attractions in Windham County:

Magic Mountain Ski Resort
Viking Nordic Centre
Stratton Golf School

Can I find two-bedroom holiday homes in Windham County?

Take off with your besties and experience complete comfort and privacy in one of the 131 two-bedroom holiday properties Windham County has to offer.

Are there holiday homes with WiFi in Windham County?

Whether you want to keep up with the latest headlines, send some emails or update your social media accounts, there are 325 holiday homes with WiFi in Windham County. Check the “WiFi” box when searching on Stayz and stay connected on your getaway.

How old do you have to be to rent a holiday home in Windham County?

The minimum age allowed can differ across properties on Stayz, so be sure to look at the rules of the holiday home in Windham County you want to book. But typically, it’s 16, 18 or 21.

How long can I rent a holiday home in Windham County for?

The length of time you can book a holiday home in Windham County is up to the property. Just enter your preferred dates to see a list of options offering extended stays. With plenty of amenities such as air conditioning and kitchens, as well as some offering weekly or monthly discounted prices, you’re sure to find someplace just right to call your home away from home in Windham County.