Windham County Vacations & Trips from $760
Book a Hotel + Flight or Car together to unlock savings
Photo by Bruce Altobelli
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Deerfield Valley Inn
Price was $882, price is now $824 per person
$824
per person
Feb 23 - Feb 25
found 1 day ago
Roundtrip flight included
Orange County (SNA) to Springfield (VSF)
9.6/10 Exceptional! (84 reviews)
Oz, Deerfield's host and owner, is simply 'ozsome.' Simply put. Feels like a second home away from home. Classic Vermont. Romantic fireplaces. And a very welcoming and friendly no-nonsense vibe throughout. Great value and convenience realized whenever in the Dover and Mt. Snow environs. Highly recommend this classic inn.
Reviewed on Jan 9, 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
The Black Bear Lodge at Stratton Mountain Resort
5 Village Lodge Road Stratton VT
$190 nightly
The price is $209 total per night from Jan 26 to Jan 27
$209 total
Jan 26 - Jan 27
Total with taxes and fees
7.4/10 Good! (945 reviews)
Place definitely needs some updating but it was clean and the staff was great!
Reviewed on Dec 18, 2025
Mount Snow Grand Summit Resort
89 Grand Summit Way West Dover VT
$336 nightly
The price is $369 total per night from Feb 2 to Feb 3
$369 total
Feb 2 - Feb 3
Total with taxes and fees
8.6/10 Excellent! (249 reviews)
Ski slopes were accessible and pool was really nice.
Reviewed on Dec 27, 2025
The Covered Bridge Inn
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $83 total per night from Jan 26 to Jan 27
$83 total
Jan 26 - Jan 27
Total with taxes and fees
7.6/10 Good! (1,003 reviews)
Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street.
Reviewed on Dec 21, 2025
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.
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Windham County
- Vacations and getaways similar to Windham County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
