Windsor County Vacations & Trips from $862
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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 Windsor County Vacation
With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.
Top destinations in Windsor County
Woodstock
Ludlow
White River Junction
Quechee
Norwich
Cavendish
Chester
Springfield
Plymouth
The Latest Windsor 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
$862
per person
Nov 6 - Nov 12
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.6/10 Excellent! (878 reviews)
Everything was great, inside and outside clean and well-maintained. Air conditioner did not work well. Room wasn't hot, but not cool either - only issue we have. We would stay again.
Reviewed on Aug 19, 2026
Mountain Green Resort
$3,634
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 Windsor County Vacation Packages
Windsor County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rutland Southern Vermont Regional Airport (RUT) |
Top Sights | Buttermilk Falls, Echo Lake and Lake Rescue |
Windsor County Hotel Deals
Align Inn Vermont
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
$110 nightly
$121 total
Aug 25 - Aug 26
Total with taxes and fees
9.4/10 Exceptional! (1,294 reviews)
"We were a little disappointed with our room compared to what we saw online. The hotel onlined appear up to date and fairly luxurious. The hotel lobby was very nice and breakfast was great. Our room was clean but very basic and not very "homey" or warm. It could use a little updating. My husband also ..."
Reviewed on Aug 21, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$449 nightly
$494 total
Sep 7 - Sep 8
Total with taxes and fees
9.4/10 Exceptional! (598 reviews)
"Amazing! Will visit again."
Reviewed on Aug 7, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road Brownsville VT
Fully refundable
$133 nightly
$145 total
Aug 23 - Aug 24
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 Windsor County attractions
Okemo Mountain Resort
9.2/10 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this romantic area.
Photo by Mike Gauthier
Quechee Gorge Bridge
9.2/10 (580 reviews)
Quechee Gorge Bridge is just one of the places to see in White River Junction, so why not enjoy the other things to explore during your travels? Wander the riverfront in this quaint area.
Photo by George Sykes
King Arthur Baking Company
9.4/10 (178 reviews)
You can enjoy retail therapy at King Arthur Baking Company during your stay in Norwich. While you're in the area, stroll along the riverfront.
Photo by Ed Gaffny
Quechee Gorge Village
9.0/10 (288 reviews)
You can enjoy retail therapy at Quechee Gorge Village during your trip to Quechee. Amble around the area's riverfront or seek out the ski slopes.
Billings Farm and Museum
9.2/10 (84 reviews)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.
Photo by William E Berry Jr.
Mount Ascutney
8.8/10 (27 reviews)
Commune with nature and explore the great outdoors at Mount Ascutney during your travels in Brownsville. You can seek out the ski slopes while in the area.
Simon Pearce Mill
9.0/10 (80 reviews)
Learn about the local history of Quechee when you spend time at Simon Pearce Mill. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
Upper Valley Aquatic Center
8.0/10 (43 reviews)
Enjoy a stop at Upper Valley Aquatic Center, an entertaining place to visit in White River Junction. Wander the riverfront in this quaint area.
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Windsor County
- Vacations and getaways similar to Windsor 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.
