Windham County Vacation Rentals, Vermont: homes, house rentals & more

Select from 656 houses, 66 apartments, and other vacation rentals to find the perfect place for your stay in Windham County. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Popular Windham County destinations on Vrbo

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!

Find spaces that suit your style

Find the best place to stay - Windham County

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30 · 9 bedrooms · 4+ bathrooms

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

Sleeps 4 · 2 bedrooms · 1 bathroom

Top rated rentals - Windham County

Premier Host

Highly recommend and a wonderful stay!

The captivating area of Windham County awaits your stay

The area's entertainment and monuments are just a few of the reasons to vacation in Windham County. Renowned for its skiing, shopping and snowboarding, this city welcomes all visitors. With a vacation 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

Do you want to find top things to see and do during your stay? Travelers enjoy Windham County for its skiing, snowboarding and hiking. Venture out of your cozy vacation rental and experience everything that Windham County has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

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)
Stratton Mountain Resort (15 mi / 24.2 km)

Exploring the mountains and other natural features in Windham County

Whether you're looking for adventure or just want to appreciate the scenery, Windham County is a great place to get outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city center:

Brattleboro Common (10.1 mi / 16.3 km)
Madame Sherris Castle Ruins (10.8 mi / 17.4 km)
Lake Raponda (11.2 mi / 18.1 km)
Spofford Lake (11.9 mi / 19.1 km)
Jamaica State Park (13.6 mi / 21.8 km)
Lowell Lake State Park (17.3 mi / 27.9 km)

Transportation 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 vacation rental?

One of the more in-demand areas to book your vacation 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 vacation rental accommodation in Windham County?

The most desirable types of vacation rentals in Windham County are houses. Looking for something different? Vrbo has plenty of options to match the needs of our guests, so you'll see vacation 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 vacation rental in Windham County?

The average price for a vacation 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 vacation 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 Vrbo 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 rental amenities in Windham County?

The most popular rental 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, Vrbo vacation homes feature the best amenities for fun and relaxation with the people you love.

Are there large group vacation rentals in Windham County?

With 326 vacation rentals that can sleep 10 guests or more in Windham County, there's no need to leave anyone off your guest list. From family vacations to special events like birthday and Christmas parties, Vrbo will help you find a large group rental 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 Center
Stratton Golf School

Can I find two-bedroom vacation rentals in Windham County?

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

Are there vacation rentals 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 vacation homes with WiFi in Windham County. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How old do you have to be to rent a vacation rental in Windham County?

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

How long can I rent a vacation rental in Windham County for?

The length of time you can book a vacation rental 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.