Chester, VT
Travel Guide
Visit Chester
Where to stay in Chester
Find the best Chester areas and neighborhoods for the activities you enjoy most. Learn more about Chester
Learn more about Chester
Chester Depot
If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.
Stone Hearth Inn and Eatery
698 VT-11 Chester VT
The price is ₩281,049 per night from Sep 9 to Sep 10
₩281,049
₩306,343 total
Sep 9 - Sep 10
includes taxes & fees
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (123 reviews)
"We had a lovely stay at Stone Hearth Inn! Very quaint place and comfortable, clean accommodations. Beautiful grounds around the property with outside seating to enjoy the fresh air. The dinner we had at the attached “Eatery” was awesome!!! So was the amazingly delicious included breakfast. Vickie ..."
Reviewed on Aug 30, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is ₩711,770 per night from Sep 14 to Sep 15
₩711,770
₩842,149 total
Sep 14 - Sep 15
includes taxes & 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. ...
9.4/10 Exceptional! (603 reviews)
"Beautiful property, really special! Easy walk to shops."
Reviewed on Sep 7, 2026
Latchis Hotel
50 Main Street Brattleboro VT
The price is ₩144,140 per night from Sep 9 to Sep 10
₩144,140
₩158,553 total
Sep 9 - Sep 10
includes taxes & fees
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (976 reviews)
"Considering the age of the property, this is a great stay! The staff was super helpful upon arrival, helping with check-in, parking and directions. The proximity to shops and restaurants is amazing. The room was clean and comfortable. I love that there were extra fans in the room to account for the ..."
Reviewed on Sep 5, 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.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3387 East Mountain Road Killington VT
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage ...
9.2/10 Wonderful! (68 reviews)
"It was pet friendly and also was quite and relaxing"
Reviewed on Sep 8, 2026
Fat Sheep Farm & Cabins
122 Best Rd Windsor VT
Stay at this cabin in Windsor. Enjoy free WiFi, free parking, and a garden. Popular attractions Hartland Public Library and Path of Life Garden are located ...
9.8/10 Exceptional! (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views!"
Reviewed on Jan 5, 2026
Long Trail House at Stratton Mountain Resort
761 Stratton Access Rd Stratton VT
Book a stay at this ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.6/10 Excellent! (83 reviews)
"Great location - the room was very clean and spacious. You don't check in at the property but at another one nearby. Hot tub was nicely maintained"
Reviewed on Jan 31, 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.
