4/5 - Good
Verified traveler
Interesting histroy!
Visit Windsor
Fat Sheep Farm & Cabins
122 Best Rd Windsor VT
$195 nightly
The price is $213 total per night from Nov 18 to Nov 19
$213 total
Nov 18 - Nov 19
Total with taxes and fees
Stay at this 3-star farm stay in Windsor. Enjoy free WiFi, free parking, and a garden. Popular attractions Hartland Public Library and Path of Life Garden are ...
9.6/10 Exceptional! (11 reviews)
An absolutely stunning property! The cabin was clean, well stocked and perfectly located to see the gorgeous sunrise. So very grateful for our quick trip at Fat Sheep Farm. Looking forward to returning!
Reviewed on May 6, 2025
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
$147 nightly
The price is $161 total per night from Nov 20 to Nov 21
$161 total
Nov 20 - Nov 21
Total with taxes and fees
Book a stay at this ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,003 reviews)
We love it here.
Reviewed on Nov 15, 2025
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (548 reviews)
I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn
Reviewed on Nov 4, 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.
Mountain Green
133 E Mountain Rd Killington Killington VT
Stay at this condo in Killington. Enjoy free parking, a picnic area, and an indoor pool. Popular attractions Killington Resort and Pico Mountain at Killington ...
6.4/10 (13 reviews)
Great communication from Jeff.
Reviewed on Sep 25, 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3387 East Mountain Road Killington VT
Stay at this 3-star ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage ...
9/10 Wonderful! (53 reviews)
Arrived after dark. Didn’t know where to park. Very secluded. Outside light would not stay lit. Upstairs needs attention.
Reviewed on Oct 27, 2025
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Ludlow VT
Book a stay at this ski condo in Ludlow. Enjoy laundry facilities, ski-in/ski-out access, and patios. Popular attractions Okemo Mountain Resort and Skywalker ...
8.8/10 Excellent! (40 reviews)
Hallway temp was WAY too hot as was temp in condo with no way to adjust thermostat.Directions to parking lot unclear and could not find back up lock box. Fortunately someone from VaCasa was able to assist with access. Was at property for a Hill Climb event outside of ski season so cannot rate how ...
Reviewed on Oct 26, 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
4.5/5(5 reviews)
You can take time to visit Harpoon Brewery during your travels to Windsor. Wander the forest or discover the area's mountain views.
American Precision Museum
You can spend time exploring the galleries in American Precision Museum in Windsor. Wander the riverfront in this quaint area.
Mt Ascutney Hospital and Health Center: Primary Care - Windsor
Though Mt Ascutney Hospital and Health Center: Primary Care - Windsor might be what brings you to town, perhaps you'll have a chance to explore more of Windsor while you are here.
Ascutney Park
Ascutney Park is just one of the places to see in Ascutney, so why not enjoy the other things to explore during your travels? Discover the mountain views while you're in the 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.
The Sustainable Farmer
Enjoy an outing to The Sustainable Farmer during your stay in Windsor. Wander the riverfront in this quaint area.
Reviews of Windsor
4.6
Top Destination
5/5 - Excellent
Verified traveler
Visit Windsor’s Main Street and don’t miss getting a maple creamy and peeking in the historic bank vault.
5/5 - Excellent
Verified traveler
The new management took over the property since beginning of August. I have never seen owners so dedicated to every single guest and trying to accommodate everyone's needs. Andy and Jossy were absolutely amazing.
5/5 - Excellent
Verified traveler
Such an amazing place to stay!
4/5 - Good
Verified traveler
We visited over New Year's weekend which limited what was opened. The train station is now a restaurant where we had dinner one evening. The food was great as well as the atmosphere. I would highly recommend it.
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