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Top Cities in Windham County

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Our top choices for Windham County hotels

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort
3.0 star property
West Dover
8.8 out of 10, Excellent, (243)
"Great place to stay!"
United States
Sonia
The price is RM654
RM783 total
includes taxes & fees
11 Dec - 12 Dec
Mount Snow Grand Summit Resort

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, (940)
"We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses."
United States
Mark
The price is RM762
RM921 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Black Bear Lodge at Stratton Mountain Resort

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is RM326
RM359 total
includes taxes & fees
13 Dec - 14 Dec
The Covered Bridge Inn

Mountaineer Inn

Mountaineer Inn
2.0 star property
West Dover
8.6 out of 10, Excellent, (550)
"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

Econo Lodge Brattleboro

Econo Lodge Brattleboro
2.0 star property
Brattleboro
5.4 out of 10, (601)
"Room was dirty, tv was tiny..very poor value"
United States
Raymond
The price is RM213
RM235 total
includes taxes & fees
16 Dec - 17 Dec
Econo Lodge Brattleboro

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (89)
"Great place for a quick trip to VT!"
United States
Rory
The price is RM534
RM587 total
includes taxes & fees
11 Dec - 12 Dec
Chalet 239

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 RM686
RM755 total
includes taxes & fees
17 Dec - 18 Dec
Big Bears Lodge

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (925)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is RM589
RM648 total
includes taxes & fees
30 Dec - 31 Dec
Hampton Inn Brattleboro

The White House Inn

The White House Inn
3.5 star property
Wilmington
9.2 out of 10, Wonderful, (260)
"The room was beautiful and the historic charm was wonderful "
United States
Karin
The price is RM682
RM750 total
includes taxes & fees
4 Jan - 5 Jan 2026
The White House Inn

Valley Craft Ales

Valley Craft Ales
2.0 star property
Wilmington
8.4 out of 10, Very good, (183)
"Fun place to stay!!"
United States
Brian
Valley Craft Ales

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1000)
"Nice motel. "
United States
Richard
The Putney Inn

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (736)
"Reasonable rate for the the accomadations."
United States
David
The price is RM293
RM322 total
includes taxes & fees
16 Dec - 17 Dec
Travelodge by Wyndham Brattleboro VT

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very good, (835)
"Great stay"
United States
Jason
The price is RM537
RM591 total
includes taxes & fees
11 Dec - 12 Dec
Latchis Hotel

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 RM494
RM543 total
includes taxes & fees
11 Dec - 12 Dec
Colonial Motel And Spa

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is RM1,627
RM2,023 total
includes taxes & fees
11 Dec - 12 Dec
Long Trail House at Stratton Mountain Resort

Inn At Mount Snow

Inn At Mount Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (51)
"From start to finish the staff could not do enough for you and the quality of the inn was amazing"
United Kingdom
Andrew
The price is RM549
RM604 total
includes taxes & fees
16 Dec - 17 Dec
Inn At Mount Snow

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 RM1,215
RM1,511 total
includes taxes & fees
11 Dec - 12 Dec
Vantage Point Villas at Stratton Mountain Resort

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (86)
"We had a lovely time staying here. "
United States
Jeff
Deerfield Valley Inn

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (738)
"Staff was friendly and pool was nice"
United States
Joshua
The price is RM475
RM522 total
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn & Suites Brattleboro I-91

The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
2.5 star property
Londonderry
8.2 out of 10, Very good, (686)
"Wery good diner"
United States
Yelena
The price is RM410
RM455 total
includes taxes & fees
14 Dec - 15 Dec
The Upper Pass Lodge at Magic Mountain
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.
Showing deals for:19 Dec - 21 Dec
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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 RM235 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 RM235 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!