Windham County Vacations & Trips from $722
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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
Brattleboro
The Latest Windham County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Killington Mountain Lodge, Tapestry Collection by Hilton
Price was $1,138, price is now $902 per person
$902
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
Wonderful experience definitely would stay again.
Reviewed on Dec 16, 2025
Jackson Gore Village
Jackson Gore Base Area
Price was $1,431, price is now $1,155 per person
$1,155
per person
Mar 5 - Mar 9
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
The hotel has great location, clean, staff friendly. First ski lift by the hotel has old used seats. You are getting cold by sitting on this right away.
Reviewed on Dec 20, 2025
Winterplace at Okemo
Clock Tower Base Area
Price was $1,555, price is now $1,285 per person
$1,285
per person
Mar 5 - Mar 9
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.8/10 Excellent! (25 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on Dec 1, 2025
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 |
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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.
