Windsor County Vacations & Trips from $962
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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
The Latest Windsor County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
$3,993
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9.2/10 Wonderful! (68 reviews)
Property was good. We founded a lot of cobble webs around the house. The stove was dirty when we used and made a horrible smell of burned. The guys next door were very loud at 3am and we couldn't sleep till they left around 5-6am. Will for sure be back if we have a chance. The place is well located around town and near lot os restaurants e attractions.
Reviewed on Oct 5, 2026
Mountain Green Resort
$4,190
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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
$1,546
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9/10 Wonderful! (884 reviews)
The mattress sunk in the middle so bad that we were crushed together and my wife couldn’t even sleep in the bed. I’m still upset with the fact they didn’t mention there was no elevator in our unit. 24 steps up for two 70 year old people is not something I would recommend to anyone.
Reviewed on Sep 29, 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
$115 nightly
$126 total
Nov 1 - Nov 2
Total with taxes and fees
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$479 nightly
$527 total
Nov 2 - Nov 3
Total with taxes and fees
9.4/10 Exceptional! (614 reviews)
"Clean rooms, very friendly staff, noise AC"
Reviewed on Oct 5, 2026
Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
$199 nightly
$219 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (916 reviews)
"Everything about this property was exceptional, EXCEPT the bed. We had an amazing time, enjoyed the lift to view fall colors & mountain coaster. But we had a miserable experience sleeping. The beds are like rock. I know it's the granite state, but get some toppers!"
Reviewed on Oct 6, 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.
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