Chester, VT
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 ￥63,845 per night from Sep 7 to Sep 8
￥63,845
￥77,098 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. ...
9.4/10 Exceptional! (602 reviews)
"Beautiful as is the town"
Reviewed on Sep 3, 2026
Latchis Hotel
50 Main Street Brattleboro VT
The price is ￥17,418 per night from Sep 8 to Sep 9
￥17,418
￥19,160 total
Sep 8 - Sep 9
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! (974 reviews)
"Great place. Staff are very nice and helpful."
Reviewed on Sep 1, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
The price is ￥24,637 per night from Sep 7 to Sep 8
￥24,637
￥29,486 total
Sep 7 - Sep 8
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
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Mount Holly VT
Stay at this cabin in Mount Holly. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and Lake Ninevah are located ...
9.8/10 Exceptional! (254 reviews)
"We have returned to this property multiple times. It's our favorite place to stay when we visit Vermont. The booking/check-in/check-out process is so quick and painless. The cabin is always in great condition; clean, tidy, and stocked with essentials. The cabin is located in a great area. It is tucked ..."
Reviewed on Sep 2, 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.
Stay near popular Chester attractions
Things to do
Colonial Flintlock Musket Experience
￥20,590
per adult
100% of travellers recommend
