Windham County Vacations & Trips from $532
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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
Stratton
Brattleboro
West Dover
Wilmington
Whitingham
Londonderry
Putney
The Latest Windham County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Grand Summit Resort, A Vail Resorts Property
$532
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (300 reviews)
We need to change room because my husband is physically handicapped and the queen size bed wasn't working for us. They were wonderful about getting us another room. Very helpful and understanding. We will definitely stay there again.
Reviewed on Aug 16, 2026
The Shire Woodstock
$1,830
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (969 reviews)
The staff was helpful. The room was clean. There was some 1st floor construction that it would have been nice to know about prior to check in. It didn’t impact our stay but made things a bit dusty. Very conveniently located to downtown area.
Reviewed on Aug 13, 2026
Mountain Green Resort
$3,024
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
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
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$114 nightly
$126 total
Aug 20 - Aug 21
Total with taxes and fees
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$116 nightly
$128 total
Sep 8 - Sep 9
Total with taxes and fees
8.2/10 Very Good! (1,010 reviews)
"The pool need more cleaning."
Reviewed on Aug 16, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$75 nightly
$82 total
Aug 18 - Aug 19
Total with taxes and fees
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.
Stay near popular Windham County attractions
Stratton Mountain Resort
9.2/10 (365 reviews)
Spend days outside on the mountain slopes and evenings eating in the picturesque village and relaxing in cozy mountainside lodging.
Photo by Doug Blackmore/Mount Snow
Mount Snow
9.2/10 (568 reviews)
Perform wild tricks on a world-class terrain park or cruise down scenic blue-graded runs at this Green Mountain ski resort in West Dover.
The Stone Church
8.6/10 (39 reviews)
After visiting The Stone Church, make a plan to see the other sights and activities in Brattleboro. While you're here, you can savor the top-notch restaurants.
Magic Mountain Ski Resort
8.6/10 (74 reviews)
Hit the slopes in Londonderry with a visit to Magic Mountain Ski Resort. Discover the mountain views in this quaint area.
Stratton Mountain Summit Gondola
9.4/10 (98 reviews)
Enjoy a trip to Stratton Mountain Summit Gondola and popular activities like skiing in Stratton. Discover the mountain views in this quaint area.
Vermont Country Store
9.2/10 (382 reviews)
Enjoy an outing to Vermont Country Store during your stay in Rockingham. You can seek out the ski slopes while in the area.
Vermont Marketplace
10.0/10 (1 review)
You can browse for the perfect souvenirs at Vermont Marketplace during your visit to Brattleboro. While you're here, you can savor the top-notch restaurants.
Lake Raponda
9.6/10 (10 reviews)
Commune with nature and explore the great outdoors at Lake Raponda during your travels in Wilmington. While you're here, you can savor the top-notch restaurants.
What to do in Windham County
Vermont RT 100 App-Guided Driving Audio Tour
$17
per traveler
Mindful Forest Escape: Rebalance, reflect and connect
$95
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
