Discover a selection of 1,500 vacation rentals in Windham County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $64 per night, and houses and condos are popular options for a stay in Windham County. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Windham County
Destination guide

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. Mount Snow and Stratton Mountain Resort are just a couple of the must-sees. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

Things to do

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 (13.5 mi / 21.7 km)
  • Stratton Mountain Resort (15 mi / 24.2 km)
  • Okemo Mountain Resort (28.9 mi / 46.5 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)
Natural features

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)
  • Spofford Lake (11.9 mi / 19.1 km)
  • Jamaica State Park (13.5 mi / 21.7 km)
  • The Ledge (15.2 mi / 24.5 km)
  • Lye Brook Falls (21.8 mi / 35.1 km)
  • Battenkill River (23.7 mi / 38.2 km)
How to get there

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.

What are the top vacation rentals in Windham County?

From luxury houses to intimate cottages, Vrbo has properties to fit all budgets and tastes. Here are some of the top vacation rentals in Windham County:

  • "Grafton Village Haven": If you're after somewhere in Grafton with 1 bedroom and plenty of style, this retreat will tick your boxes. Amenities include air conditioning and a kitchen.
  • "True Ski In/ski Out 3 Bedroom End Unit Directly On Mount Snow": Located in Liscia di Vacca, this popular getaway has 3 bedrooms and plenty of handy amenities. Shopping and a games room are just a couple you'll find here.

For even more great options, use the search bar at the top of the page to find the perfect Windham County vacation rental for you.

What are the best tiny house vacation rentals in Windham County?

You need only take a peek inside our tiny house vacation rentals in Windham County to discover that good things really do come in little packages. Sensibly designed to maximize every square inch of space, these pocket-sized digs deliver a big vacation experience:

  • Get away from it all and get back to basics at "Cheerful Tiny Home Cabin Near Hiking". This retreat in Townshend packs plenty of comforts into its compact space, such as off-street parking options and towels.
  • Alternatively, make yourself at home at "Cozy Lakeside Tiny Home, Near Skiing". Located in Whitingham, this wee gem comes with a phone and a kitchen.

Can I find log cabins to rent in Windham County?

Often set in secluded natural locations, log cabins offer a cozy escape from the busyness of everyday life. If you're ready to switch off and unwind, check out these log cabins to rent in Windham County:

  • Located in Newfane, "Vermont Log Cabin With Amazing Views" will put you close to some of the fabulous outdoor activities offered in this area. Kayaking and cycling are among them.
  • Alternatively, get your vacation on at "Beautiful, Private Log Cabin With Huge". Try some mountain biking or skiing or simply put your feet up at this Townshend retreat.

What are the top-rated vacation rentals for weekend getaways in Windham County?

There's nothing more exciting than getting in the car and traveling to somewhere new. If you'd like to get away and put your feet up for a few days, check out these weekend getaways in Windham County:

  • "True Ski In/ski Out Updated 3 Bedroom End Unit Directly On Mount Snow" in West Dover is a great choice if you adore the outdoors. Get out and see the area's best nature attractions, like Magic Mountain Ski Resort and Lye Brook Falls, or try some activities. Tennis and golf will keep you busy around these parts.
  • You'll be able to squeeze so much into your quick break at "Mt. Snow Area Private Estate On 100 Acres W". This retreat is located in Medulin and is within reach of exceptional sights like Wild Wings Ski Touring Center and Lake Raponda. Sledding and horse riding are some fun experiences that are also on your doorstep.

Can I find studio apartments for rent in Windham County?

Easy to keep clean and with everything you need within arm's reach, studio apartments are a terrific option if you're traveling alone or with a buddy. If you're looking for somewhere small and comfortable to call home for a few days, check out these studio apartments for rent in Windham County:

  • "Grafton Village Haven" in Grafton puts you close to some of the area's sought-after cultural attractions, including The Stone Church and Gander Gallery. A microwave oven and a garden are a couple of the amenities you'll have at hand here.
  • Located in Brookline, "Sunny Dog - Friendly Cabin With Firepit" is another great base for your adventure. When you've finished checking out hot spots like Jim McGrath Gallery and Studio and DaVallia Art & Accents, make use of internet services and nearby birdwatching activities back at your studio apartment.

Can I find short term rentals in Windham County?

If you're short on time but have itchy feet, there are loads of short-term rentals in Windham County where you can spend a couple of days discovering the sights. Here are just two getaways that'll help you scratch your travel itch:

  • "True Ski In/ski Out Updated 3 Bedroom End Unit Directly On Mount Snow" in West Dover is a handy place to base yourself for an action-packed stay. Settle in here and you'll be close to top sights including Mount Snow.
  • "Mt. Snow Area Private Estate On 100 Acres W" is also a favorite with guests planning a quick adventure. Book a stay at this vacation rental in Medulin to be within easy reach of The Greenwood School and other sights around town.

What are the best romantic weekend getaways in Windham County?

Whether you've been with each other for a few months, a year or an eternity, there's nothing like a romantic weekend getaway to stoke the flames of love. If you're after someplace idyllic to spend a few days with your other half, check out these retreats:

  • Enjoy some "us time" at "Grafton Village Haven". This Grafton vacation rental is made for romance, with amenities like skiing facilities and shopping facilities to help set the mood.
  • Another tempting option is "True Ski In/ski Out 3 Bedroom End Unit Directly On Mount Snow" in Liscia di Vacca. Enjoy perks here including winery tours and a fireplace, as well as each other's company.

What are the best large group vacation rentals in Windham County?

If your idea of a dream getaway is to bring along all your besties, you're going to need a whole lot of space. Luckily, there are plenty of vacation rentals in Windham County that are designed for large groups, starting with these sprawling stunners:

  • "True Ski In/ski Out 3 Bedroom End Unit Directly On Mount Snow": With 3 bedrooms, this popular option in Liscia di Vacca has more than enough room for you and all your friends and family. Amenities like ski-in/ski-out facilities and a swimming pool are on hand to make things nice and comfy.
  • "Mt. Snow Area Private Estate On 100 Acres W": You'll get your team's seal of approval at this option in Medulin which comes with mountain views, a sauna and more. It has 10 bedrooms that will easily house any large group.

What are the best houses for rent with a pool in Windham County?

Take your pick and dive right in. Here are a few sought-after house rentals in Windham County where awesome memories are made at the pool:

  • Spend your vacation at "Mount Snow Post And Beam House", where the first item on your to-do list should be pool time. This escape is located in Marlboro and offers a host of family-friendly amenities, including a dishwasher and a video library.
  • Roll out of bed and enjoy an early morning dip at "New To Market - Beautiful And Spacious House By Mount Snow" in West Dover. Skiing facilities and books are just two of the many amenities at this equally impressive option.

What are the best large family vacation rentals in Windham County?

Family time is precious time, which is why we'll help you find somewhere you can truly connect. Whether you're planning a trip with the kids or a reunion with relatives, these large family vacation rentals in Windham County are just the thing for unforgettable get-togethers:

  • Located in Liscia di Vacca, "True Ski In/ski Out 3 Bedroom End Unit Directly On Mount Snow" has 3 bedrooms and can fit up to 12 guests. Amenities include a fridge and a living room.
  • "True Ski In/ski Out Updated 3 Bedroom End Unit Directly On Mount Snow" in West Dover will also lay out the welcome mat for you and your group. Accommodating up to 11 people, this property features 3 bedrooms, a nearby laundromat and a microwave oven.

If you're on the hunt for fun family attractions in Windham County, Adams Family Farm is on many travelers' to-do lists.

Explore destinations around Windham County

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