Chester
Travel Guide
Visit Chester
Where to stay in Chester
Find the best Chester areas and neighborhoods for the activities you enjoy most.
Chester Depot
If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is CA $569 per night from Sep 7 to Sep 8
CA $569
CA $687 total
Sep 7 - Sep 8
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. ...
Latchis Hotel
50 Main Street Brattleboro VT
The price is CA $197 per night from Aug 31 to Sep 1
CA $197
CA $216 total
Aug 31 - Sep 1
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! (970 reviews)
"The hotel was very clean and the bed quite comfy. The only downside was insufficient parking. We had to use the adjacent lot but then had to leave there by 9:00 am. We ended up having to buy time to park which wasn’t a lot of money but was a bit of an irritant. Would def stay there again!"
Reviewed on Aug 29, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
The price is CA $208 per night from Sep 29 to Sep 30
CA $208
CA $250 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski ...
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.
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Chester VT
Stay at this cabin in Chester. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial ...
9.8/10 Exceptional! (25 reviews)
"This is an adorable and cozy cabin surrounded by nature - from which you can hear a soothing stream from your window. If you are looking for a place to restore in nature and unplug "glamping-style" - yet close to shops/coffee/outings, etc., - this little blue cabin is the perfect spot. I liked that ..."
Reviewed on Jul 6, 2026
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! (67 reviews)
"Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night."
Reviewed on Aug 15, 2026
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish VT
Stay at this cabin in Cavendish. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Phineas Gage Memorial and Mount Ascutney are located ...
10/10 Exceptional! (53 reviews)
"The cabins are a great getaway, stocked with everything you need for a comfortable stay in the woods. They have nice kitchens and comfortable beds, heat and AC, outdoor grills and firepits. The hot tub is a great way to relax after a day of hiking or skiing."
Reviewed on Aug 24, 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.
