Windsor Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by mike dobias
Top hotels in Windsor
Fat Sheep Farm & Cabins
122 Best Rd Windsor VT
9.6/10 Exceptional! (12 reviews)
The fat sheep farm is such a a cute cozy place. We partook in morning chores with Jay, she is absolutely amazing. She made everyone feel at home with interacting with the sheep. She was very knowledge and you can tell she genuinely loves the animals. Todd and Suzy are amazing as well. We breifly ...
Reviewed on 10 Nov 2025
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is 3.871.616 ₫ per night from 25 Nov to 26 Nov
3.871.616 ₫
4.258.778 ₫ total
25 Nov - 26 Nov
includes taxes & fees
7.2/10 Good! (1,003 reviews)
We love it here.
Reviewed on 15 Nov 2025
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is 8.678.033 ₫ per night from 30 Nov to 1 Dec
8.678.033 ₫
10.706.424 ₫ total
30 Nov - 1 Dec
includes taxes & fees
9.2/10 Wonderful! (550 reviews)
Clean room, Awesome staff and always a good vibe.
Reviewed on 17 Nov 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.
Popular places to visit
Harpoon Brewery
You can take time to visit Harpoon Brewery during your travels to Windsor. Wander the forests or discover the area's mountain views.
American Precision Museum
You can spend time exploring the galleries in American Precision Museum during your travels in Windsor. Wander the riverfront in this quaint area.
Brownsville Trail
You can take time to visit Brownsville Trail during your travels to Windsor. Discover the mountain views in this family-friendly area or seek out the ski slopes.
