Chester Travel Guide
Tourist Guide
Visit Chester
Where to stay in 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.
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is NZ$722 per night from 30 Nov to 1 Dec
NZ$722
30 Nov - 1 Dec
includes taxes & fees
Stay at this 4.5-star 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! (546 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 4 Nov 2025
The Shire Woodstock
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (875 reviews)
Great place to stay
Reviewed on 3 Nov 2025
Jackson Gore Village
111 Jackson Gore Road, Ludlow, VT
The price is NZ$452 per night from 23 Nov to 24 Nov
NZ$452
23 Nov - 24 Nov
includes taxes & fees
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (828 reviews)
The room overall was nice. There were lots of marks on the walls and baseboards. However everything was pretty clean and the fireplace was a nice touch. Unfortunately due to the time of the year we were on our own for food. I wish they told us this ahead of hour stay. Otherwise it was a nice.stay. ...
Reviewed on 29 Oct 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.
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Chester
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! (23 reviews)
Hidden gem!
This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!
Reviewed on 24 Feb 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 27 Oct 2025
Long Trail House at Stratton Mountain Resort
761 Stratton Access Rd, Stratton, VT
Stay at this 3-star ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.4/10 Very Good! (76 reviews)
Nice lodge. Room needs updating
Reviewed on 19 Oct 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
DaVallia Art & Accents
Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.
Bonnie's Bundles Dolls
Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views or seek out its ski slopes.
