Windham County Vacations & Trips from $403
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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
The Latest Windham County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was $491, price is now $403 per person
$403
per person
Jun 27 - Jun 30
found 17 hours ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (853 reviews)
I’ve stayed here with my two daughters multiple times and it’s always incredible.
Reviewed on May 17, 2026
The Shire Woodstock
Price was $1,528, price is now $1,161 per person
$1,161
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Springfield (VSF)
8.8/10 Excellent! (929 reviews)
Lovely hotel with views of river and walkable to variety of shops and restaurants
Reviewed on May 12, 2026
Golden Stage Inn B&B
Price was $715, price is now $566 per person
$566
per person
Jun 27 - Jun 30
found 17 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
10/10 Exceptional! (44 reviews)
We stayed for the weekend and went skiing at Okemo. It was a 10 min drive away. The staff was very accommodating, welcoming and friendly. The food provided was delicious. We will definitely be back!
Reviewed on Mar 8, 2026
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was $1,209, price is now $991 per person
$991
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Springfield (VSF)
8.8/10 Excellent! (26 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
Solitude Village at Okemo by Vail Resorts
Clock Tower Base Area
Price was $1,090, price is now $906 per person
$906
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Springfield (VSF)
7.8/10 Good! (35 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know
Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.
Reviewed on Oct 8, 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 |
Windham County Hotel Deals
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $133 total per night from Jun 7 to Jun 8
$133 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (984 reviews)
"This is the best option in the area and we are big fans of the Hilton family of hotels (we stay there exclusively when this is an option). Everything was as expected for a Hampton Inn, including the workout room, layout of the room, and amenities. Five stars for pillows, hot water, and lack of noise. ..."
Reviewed on May 26, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $133 total per night from Jun 2 to Jun 3
$133 total
Jun 2 - Jun 3
Total with taxes and fees
8.6/10 Excellent! (886 reviews)
"Unique hotel. Very quiet - helpful staff though would’ve appreciated a paper receipt at checkout."
Reviewed on May 26, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
$164 nightly
The price is $180 total per night from Jun 9 to Jun 10
$180 total
Jun 9 - Jun 10
Total with taxes and fees
8.6/10 Excellent! (268 reviews)
"Rooms were very clean, great coffee in the room. The resort(the actual area in general )is in “mud month”. Very few restaurants and stores were open. Not the fault of the resort. Refrigerator needed to be requested. The views were spectacular and the lobby was beautiful"
Reviewed on May 2, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
