Windham County Vacations & Trips from $558

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Your Windham County Vacation

Answer the call of adventure with a tailor-made vacation package to Windham County. Wherever it is you're going and whatever you plan to do, prepare to discover a destination with plenty to offer. Kick off your trip to Windham County with a couple of nights in Wilmington visiting popular attractions like Mount Snow and Mount Snow Golf Course. Londonderry is another city that draws crowds from near and far. Magic Mountain Ski Resort and Jamaica State Park are two of the leading places to see in this destination. From the moment you book your Windham County vacation to when you get back home, Expedia has your back every step of the way.

Top destinations in Windham County

The Latest Windham County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Grand Summit Resort, A Vail Resorts Property
Sinclair Inn Bed and Breakfast

Find the Best Windham County Vacation Packages

Windham County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Albany Intl. Airport (ALB)
Top Sights
Lowell Lake State Park, Molly Stark State Park and Lake Raponda

Windham County Hotel Deals

Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $134 total per night from Jun 7 to Jun 8
$134 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (976 reviews)
Great staff. Newly updated decor

Reviewed on May 16, 2026

Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $138 total per night from May 19 to May 20
$138 total
May 19 - May 20
Total with taxes and fees
8.6/10 Excellent! (881 reviews)
Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!

Reviewed on May 15, 2026

Latchis Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Colonial Motel And Spa
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.