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Top Cities in Windham County

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Our top choices for Windham County hotels

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property
3.0 star property
West Dover
8.6 out of 10, Excellent, (247)
"Ski slopes were accessible and pool was really nice. "
United States
Claudia
The price is RM1,249
RM1,495 total
includes taxes & fees
13 Jan - 14 Jan 2026
Grand Summit Resort, A Vail Resorts Property

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (944)
"Place definitely needs some updating but it was clean and the staff was great!"
United States
Jacqueline
The price is RM749
RM907 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Black Bear Lodge at Stratton Mountain Resort

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (6)
"Clean rooms/ close to mountain/ nice experience"
United States
Morgan
The price is RM547
RM602 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hideaway Inn Mt. Snow

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1002)
"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
United States
Megan
The price is RM361
RM397 total
includes taxes & fees
29 Dec - 30 Dec
The Covered Bridge Inn

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (95)
"Great clean place. "
United States
Les
The price is RM835
RM918 total
includes taxes & fees
5 Jan - 6 Jan 2026
Chalet 239

The White House Inn

The White House Inn
3.5 star property
Wilmington
9.2 out of 10, Wonderful, (267)
"We stayed at the White House in two weekends in a row while our house was under construction. We loved that they had music until 9 and that the room was clean and the beds were comfortable. The staff made sure we had everything we needed. We would definitely recommend."
United States
Stacy
The price is RM671
RM738 total
includes taxes & fees
4 Jan - 5 Jan 2026
The White House Inn

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
The price is RM722
RM794 total
includes taxes & fees
4 Jan - 5 Jan 2026
Big Bears Lodge

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.4 out of 10, Very good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is RM1,640
RM2,039 total
includes taxes & fees
5 Jan - 6 Jan 2026
Long Trail House at Stratton Mountain Resort

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (928)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is RM595
RM654 total
includes taxes & fees
3 Jan - 4 Jan 2026
Hampton Inn Brattleboro

Mountaineer Inn

Mountaineer Inn
2.0 star property
West Dover
8.6 out of 10, Excellent, (551)
"Small but clean room. Hotel is under construction but staff was accommodating and pleasant to work with durning our travel. If traveling for work we’d stay again "
United States
Joseph
Mountaineer Inn

Valley Craft Ales

Valley Craft Ales
2.0 star property
Wilmington
8.4 out of 10, Very good, (191)
"The staff and amenities were fantastic"
United States
Matthew
Valley Craft Ales

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (155)
"It was wonderful & staff was great! I loved staying here!"
United States
Leticia
The price is RM942
RM1,099 total
includes taxes & fees
9 Jan - 10 Jan 2026
Vikings Villages Resort

Vantage Point Villas at Stratton Mountain Resort

Vantage Point Villas at Stratton Mountain Resort
3.0 star property
Stratton
8.4 out of 10, Very good, (70)
"Amazing stay - The condo was cozy and perfect for our family! "
United States
Kate
The price is RM1,235
RM1,536 total
includes taxes & fees
5 Jan - 6 Jan 2026
Vantage Point Villas at Stratton Mountain Resort

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1001)
"The room was okay for a quick stop to rest. "
United States
Janice
The Putney Inn

Inn At Mount Snow

Inn At Mount Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (53)
"Great location for an overnight stay to hit the slopes. Will definitely visit again. "
United States
Ryan
The price is RM870
RM957 total
includes taxes & fees
12 Jan - 13 Jan 2026
Inn At Mount Snow

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (737)
"Bitten up motel needs renovation definitely. "
United States
Piotr
The price is RM215
RM237 total
includes taxes & fees
31 Dec - 1 Jan 2026
Travelodge by Wyndham Brattleboro VT

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1001)
"Nice place to stay for the night."
United States
Robin
The price is RM486
RM535 total
includes taxes & fees
29 Dec - 30 Dec
Colonial Motel And Spa

Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.4 out of 10, (606)
"Room was dirty, tv was tiny..very poor value"
United States
Raymond
The price is RM266
RM293 total
includes taxes & fees
29 Dec - 30 Dec
Econo Lodge Brattleboro South

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (88)
"We had a lovely time staying here. "
United States
Jeff
Deerfield Valley Inn

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very good, (840)
"Great stay"
United States
Jason
The price is RM474
RM521 total
includes taxes & fees
29 Dec - 30 Dec
Latchis Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windham County Hotel Reviews

Guide to exploring Windham County

Top reasons to visit Windham County

  • Thrilling Ski Resorts: Windham County boasts excellent skiing opportunities at various resorts, perfect for winter sports enthusiasts.
  • Charming Art Towns: Explore delightful towns filled with art galleries and local crafts, showcasing the region's creative spirit.
  • Scenic Natural Beauty: The area offers breathtaking landscapes, including national parks and beautiful lakes, ideal for outdoor adventures.
  • Rich Historical Significance: Experience the local history, including attractions from the Civil War era, adding depth to your visit.
  • Diverse Accommodation Options: Choose from cosy cottages to luxurious inns, catering to a variety of preferences and budgets.

Find great hotels in Windham County

Discover the charming hotels of Windham County, Vermont, where adventure meets comfort. Whether you seek a family-friendly retreat, a pet-friendly getaway, or the unique experience of agritourism, this region offers a variety of lodging options. Choose from the inviting Chimney Hill, delightful cosy cottages, or the welcoming Andrews Inn, each designed to provide a memorable stay amidst the stunning natural beauty of Vermont.

  • The Black Bear Lodge at Stratton Mountain Resort: Nestled in the heart of Windham County, The Black Bear Lodge at Stratton Mountain Resort is a charming 3-star retreat perfect for families seeking a memorable vacation. The lodge features family-friendly amenities, including supervised childcare services and an exciting arcade game room, ensuring that children have a fantastic time. With its rustic décor and warm ambience, the lodge provides a welcoming atmosphere for guests to unwind after a day of exploration.
  • Mount Snow Grand Summit Resort: Embrace the thrill of adventure at Mount Snow Grand Summit Resort, a 3-star hotel that offers an exhilarating ski-themed experience. Located conveniently close to ski lifts and shuttles, this resort caters to adventure seekers with activities such as snowboarding, hiking, and mountain biking. For those looking for relaxation, the full-service spa offers an array of treatments, including Thai massages and Ayurvedic therapies, complemented by a refreshing pool service. This resort is the ultimate destination for both adventure and relaxation.
  • The Upper Pass Lodge at Magic Mountain: If you're looking for a pet-friendly adventure, The Upper Pass Lodge at Magic Mountain is the ideal choice. This motel-style accommodation blends comfort with excitement, offering various outdoor activities such as zip-lining and snowshoeing. The lodge welcomes pets, allowing you to bring your furry companions along for the ride. With nearby recreational opportunities, it’s perfect for those wanting to immerse themselves in the natural beauty and adventure of Windham County.

Where to stay in Windham County

Windham County, Vermont, offers a delightful blend of adventure and relaxation, perfect for a memorable vacation. Explore charming art towns, indulge in family-friendly activities, and enjoy the welcoming atmosphere created by friendly locals. With options ranging from budget to luxury accommodations, you can experience the best of both worlds. Don't miss the nearby attractions in Bennington County and the historical significance of the Civil War era, ensuring a rich and fulfilling travel experience.

  • Brattleboro: Nestled in the heart of Windham County, Brattleboro is a vibrant city that attracts visitors year-round, with peak seasons from July to September. Known for its exceptional skiing and adventure sports, it offers access to numerous ski resorts and fields. The stunning natural surroundings, including lakes, mountains, and the nearby national state park, provide ample opportunities for outdoor activities and exploration. Whether you're hitting the slopes or enjoying a leisurely hike, Brattleboro is a gateway to both excitement and relaxation.
  • Wilmington: Located in the picturesque Windham County, Wilmington is another charming city that invites adventure seekers. Like Brattleboro, it experiences a peak in visitor numbers during July and from September to October. The city is renowned for its skiing options, with excellent ski resorts and fields catering to winter sports enthusiasts. The breathtaking landscapes, featuring serene lakes, majestic mountains, and beautiful valleys, make Wilmington a perfect spot for outdoor adventures as well as a peaceful retreat for nature lovers.
  • Grafton: Grafton, also situated in Windham County, is a delightful destination for those searching for outdoor experiences and adventure. The city experiences a similar flow of visitors, especially peaking in July and September to October. It is famed for its skiing facilities, with numerous ski resorts and fields available for thrill-seekers. Surrounded by stunning lakes, valleys, and mountains, Grafton offers not only exhilarating winter sports but also a tranquil atmosphere for those looking to unwind and enjoy nature's beauty.

Things to do in Windham County

Windham County, Vermont, offers an exciting blend of skiing, adventure, and sports activities. Visitors can enjoy skiing at various resorts and fields, while also indulging in antique shopping and art walks. For those seeking a change of scenery, there are delightful day trips to explore the natural beauty and charm of the region. Whether you're hitting the slopes or discovering local treasures, Windham County has something for everyone.

Shopping

The Vermont Country Store offers a charming selection of local goods and unique gifts, perfect for souvenirs. At the Brattleboro Farmers' Market, you can enjoy fresh produce and artisan products. For a broader shopping experience, Vermont Marketplace combines shopping, entertainment, and family-friendly activities in a lively setting.

Recreation

At Mount Snow Golf Course, enjoy a round of golf amidst stunning landscapes, perfect for relaxation and outdoor fun. The Stone Church offers live music events, providing a vibrant atmosphere for entertainment. Brattleboro Country Club exudes luxury, making it an ideal spot for unwinding in a serene environment.

Adventure

Experience the thrill of skiing at Stratton Mountain Resort, where adventure awaits on pristine slopes. For more skiing excitement, head to Mount Snow, renowned for its diverse ski options. Take a scenic ride on the Stratton Mountain Summit Gondola, offering breathtaking views and an exhilarating ascent.

Nightlife

Experience the vibrant nightlife of Windham County at the Bellows Falls Opera House, where romance and culture intertwine. For an adventurous twist, visit Brattleboro Bowl, brimming with excitement. Don’t miss the Latchis Theatre, a charming venue that offers a captivating mix of entertainment and romance.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Windham County

For a budget-friendly visit to Windham County, consider travelling during the cheaper months of April to May and November, avoiding peak times like December to February. Tuesdays are the least expensive days for accommodation, while Fridays are the priciest. Use Expedia to search for eco-certified hotels that fit your budget and preferences, and arrange results by price to find the best deals. Additionally, save money by bundling your hotel, flights, and activities into a package. Take advantage of free local attractions to further stretch your budget while enjoying the beauty of the area.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windham County are April to May and November, where the prices are slightly lower. This is in comparison to December to February, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windham County is Tuesday. The most expensive day to stay in Windham County is Friday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified filter will reveal sustainable and environmentally-friendly hotels currently available. To find the most affordable prices and offers, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Windham County hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in Windham County

Windham County, Vermont, is a fantastic destination for ski enthusiasts and adventure seekers. With an array of attractions such as national parks, ski resorts, and beautiful lakes, it offers something for everyone. Whether you're looking for cultural experiences, outdoor activities, or family-friendly fun, you'll find plenty to explore in this charming region. It's the perfect spot for an unforgettable holiday filled with excitement and natural beauty.

  • Stratton Mountain Resort: Experience the thrill of skiing and snowboarding at one of Vermont's premier ski resorts. Stratton Mountain offers stunning outdoor adventures year-round, with picturesque trails and vibrant après-ski vibes. Ideal for both beginners and seasoned pros, it’s a winter wonderland waiting to be explored.
  • Landmark College: Immerse yourself in the dynamic atmosphere of Landmark College, a unique institution focused on innovative learning methods. With its modern facilities and urban vibe, it’s perfect for those looking to engage in educational experiences or simply enjoy the lively campus environment.
  • Molly Stark State Park: Discover the natural beauty of Molly Stark State Park, where outdoor enthusiasts can hike scenic trails and enjoy breathtaking vistas. This tranquil park is perfect for adventure lovers seeking to immerse themselves in Vermont's stunning landscapes.

The nearest major airports for your trip to Windham County

When planning your visit to Windham County, Vermont, consider flying into one of the nearby major airports. Hartford, CT (BDL-Bradley Intl.) is situated 117.5km away, with excellent accommodations such as the 4-star Simsbury 1820 House, just 11.3km from the airport. Albany, NY (ALB-Albany Intl.) is 98.2km distant, offering options like The Landing Hotel at Rivers Casino & Resort, located 12.9km away. Lastly, Manchester, NH (MHT-Manchester-Boston Regional) is 99.8km from Windham County, with the 4-star DoubleTree by Hilton Nashua available just 16.1km from the airport. These hotels provide convenient access to their respective airports for a smooth travel experience.

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Frequently asked questions

How much do hotels in Windham County cost?
The season and factors like Easter and school holidays can influence the price of a hotel in Windham County. You can find cheap options from RM237 in a few different ways on Expedia. First, select the dates you'd like to get away, then use the filters like property type and amenities to fine-tune your search. You can also sort by price, so the lowest options appear at the top.
When is the best time to go to Windham County?
If you want to visit in summer, reserve your Windham County hotel between June and August. Temperatures during the summer months here range from 12ºC to 24ºC. Windham County has a humid continental climate, so pack accordingly.
How can I find cheap hotels in Windham County?
Windham County cheap hotels start at RM237 per night. To browse these types of wallet-friendly options, make use of our "Price per night" filter. Like some other tips? Be flexible with your holiday dates and book early. Check out our cheap hotels in Windham County page for deals you won't be able to resist.
What are the best hotels in Windham County for families?
Big Bears Lodge is among the most popular hotels for families, located in Stratton, Windham County. Stay here and take advantage of amenities like a playground and complimentary breakfast. Three Mountain Inn is another favourite property where kiddos are welcome. For more hotel options, fine-tune your search results by clicking on "Family friendly" under the "Traveller experience" filter section.
Why should I book my Windham County hotel with Expedia?
Expedia is your one-stop shop for organising the ultimate holiday experience in Windham County. You'll find a wide variety of hotels to choose from and search filters that make it a breeze to find the stay of your dreams. Worried about your plans changing? Many of our hotels have flexible cancellation policies, so you can book with peace of mind. Get more out of your trip with Expedia Rewards. Join today for free and you can collect points and unlock membership perks. You'll enjoy instant access to Member Prices, which adds up to savings worth 10% or more on select hotels!