Windsor County Vacations & Trips from $631
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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
The Latest Windsor County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Lake Bomoseen Lodge
Price was $709, price is now $631 per person
$631
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (922 reviews)
Clean, convenient and friendly. Another group in my party got a fantastic surprise upgrade.
Reviewed on May 3, 2026
Vikings Villages Resort
Price was $747, price is now $669 per person
$669
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
10/10 Exceptional! (184 reviews)
Viking village is one of the most unique experiences we have had with being the most authentic and amazing Norse village in the United States. Attention to comfort and period detail along with an outdoor fire pit with Soay goats was unmatched. We didn’t want to leave. Paul and Christine were fabulous hosts and we will be back to the Viking village!
Reviewed on May 2, 2026
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was $797, price is now $720 per person
$720
per person
Jun 12 - Jun 14
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on Dec 1, 2025
Chalet 239
Price was $730, price is now $664 per person
$664
per person
Jun 12 - Jun 14
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
9.4/10 Exceptional! (124 reviews)
Only issue is there was nowhere to hang anything and the room was very small. Room was clean, comfortable and bathroom was well-appointed. Breakfast was good and staff friendly and helpful. Close to restaurants and super easy access to Mt. Snow. Would definitely stay here again.
Reviewed on Mar 28, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was $767, price is now $698 per person
$698
per person
Jun 12 - Jun 14
found 22 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (VSF)
8.6/10 Excellent! (852 reviews)
No inflatable mattress offered anymore.
Reviewed on Mar 18, 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
$115 nightly
The price is $127 total per night from May 19 to May 20
$127 total
May 19 - May 20
Total with taxes and fees
9.4/10 Exceptional! (1,185 reviews)
The Align Inn has been a welcome retreat for me while I work in Hanover during the week. The staff is very friendly and helpful, and the room is comfy clean and quiet.
Reviewed on May 5, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from May 25 to May 26
$395 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (575 reviews)
Everything was excellent
Reviewed on May 5, 2026
Hotel Coolidge
39 South Main Street White River Junction VT
Fully refundable
$108 nightly
The price is $118 total per night from May 10 to May 11
$118 total
May 10 - May 11
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
My husband and I have stayed overnight at the Hotel Coolidge on many occasions. It is conveniently located near Dartmouth-Hitchcock Medical Center. The owner and staff are always friendly, the rooms are clean, the beds are comfortable, coffee and tea are provided around the clock in the lobby, there ...
Reviewed on Apr 30, 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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