Windham County Vacations & Trips from $404
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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
Wilmington
West Dover
Brattleboro
Londonderry
Newfane
Putney
The Latest Windham County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
$404
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
New York (LGA) to Springfield (VSF)
8.6/10 Excellent! (992 reviews)
It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay.
Reviewed on Oct 21, 2026
Mountain Green Resort
$2,156
per person
Dec 31 - Jan 3
found 20 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
$169 nightly
$185 total
Nov 16 - Nov 17
Total with taxes and fees
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$99 nightly
$109 total
Nov 1 - Nov 2
Total with taxes and fees
6.2/10 (103 reviews)
"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."
Reviewed on Oct 20, 2026
Hideaway Inn Mt. Snow
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
$108 nightly
$119 total
Oct 27 - Oct 28
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.
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.
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.
Mount Snow Golf Course
8.6/10 (22 reviews)
Play a round of golf in West Dover at Mount Snow Golf Course, and enjoy other activities such as skiing. Discover the mountain views while you're in the area.
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
80% of travellers recommend
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.
