Windsor County Vacations & Trips from $524
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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
Ludlow
The Latest Windsor County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Chalet 239
Price was $895, price is now $751 per person
$751
per person
Mar 4 - Mar 8
found 12 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
9.4/10 Exceptional! (87 reviews)
Chalet 239 was awesome and completely unexpected! It's an old motel that was recently renovated and has a country charm with new decor and amenities. Everything was clean, new and beautiful. Max was excellent in keeping in touch. I will definitely stay there again!
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
$120 nightly
The price is $132 total per night from Feb 2 to Feb 3
$132 total
Feb 2 - Feb 3
Total with taxes and fees
9.2/10 Wonderful! (1,093 reviews)
Very polite staff and very clean rooms.
Reviewed on Jan 27, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$148 nightly
The price is $160 total per night from Mar 3 to Mar 4
$160 total
Mar 3 - Mar 4
Total with taxes and fees
8.8/10 Excellent! (962 reviews)
Friendly staff, clean rooms.
Reviewed on Jan 28, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night from Feb 22 to Feb 23
$384 total
Feb 22 - Feb 23
Total with taxes and fees
9.2/10 Wonderful! (561 reviews)
Excellent hotel, staff well trained.
Reviewed on Jan 21, 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.
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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.