Windsor County Holidays
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Top hotels in Windsor County
The Shire Woodstock
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (855 reviews)
Our room was clean and welcoming.
Reviewed on 16 Oct 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is €368 per night from 16 Nov to 17 Nov
€368
16 Nov - 17 Nov
includes taxes & fees
9.2/10 Wonderful! (539 reviews)
Beautiful hotel with excellent staff and room cleanliness. Red Rooster Inn had good breakfast options, however dinner was a little underwhelming and expensive. There are better options at the local fine dining restaurants.
Reviewed on 18 Oct 2025
Jackson Gore Village
111 Jackson Gore Road, Ludlow, VT
Fully refundableReserve now, pay when you stay
The price is €194 per night from 26 Oct to 27 Oct
€194
26 Oct - 27 Oct
includes taxes & fees
8.4/10 Very Good! (809 reviews)
The staff truly made the experience stand out. From check-in to check-out, everyone I interacted with was professional, friendly, and genuinely welcoming.
Reviewed on 18 Oct 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
