Windham County Vacations & Trips from $729
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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.
Mountain Green Resort
$4,036
per person
Dec 24 - Dec 31
found 6 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
$1,422
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Rutland (RUT)
9/10 Wonderful! (884 reviews)
70 year old couple got upgraded to a suite because of overbooking of the ground floor 1 bedroom unit. However the suite included 32 steps with no elevators.
Nice fire pit in the evening. No breakfast or lunch options on property.
Reviewed on Oct 10, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
$3,242
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on Jun 26, 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
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 (87 reviews)
"No hot water, and it was a known problem. They ran out of fuel for hot water heater. Couldn’t have cared less!"
Reviewed on Oct 10, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
$163 nightly
$179 total
Nov 10 - Nov 11
Total with taxes and fees
8.6/10 Excellent! (314 reviews)
"Allen in the restaurant is great."
Reviewed on Oct 6, 2026
Hideaway Inn Mt. Snow
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
$107 nightly
$117 total
Nov 3 - Nov 4
Total with taxes and fees
8.6/10 Excellent! (141 reviews)
"This place was great! Super cute and clean"
Reviewed on Oct 9, 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.
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.
