Windsor County Vacations & Trips from $873
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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
Springfield
Plymouth
Chester
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
$873
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.6/10 Excellent! (878 reviews)
Pool was nice with dry and steam sonna. Restaraunt and bar was good not a big food selection but food was good quality. Lift base was very near the facility with a lot of trails nearby
Reviewed on Aug 9, 2026
The Shire Woodstock
$1,421
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (968 reviews)
Nice place to stay was major construction going on which didn't bother us too much but might have been nice to be aware beforehand. We had a lovely room on the second floor.
Reviewed on Aug 11, 2026
Mountain Green Resort
$3,125
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
$119 nightly
$131 total
Aug 17 - Aug 18
Total with taxes and fees
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
On The River Inn
1653 West Woodstock Road Woodstock VT
$279 nightly
$307 total
Sep 1 - Sep 2
Total with taxes and fees
9.4/10 Exceptional! (1,008 reviews)
"Everything was good I cannot complain"
Reviewed on Aug 12, 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 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.
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.
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.
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.
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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.
