Chester, VT

Travel Guide

Where to stay in Chester

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Chester Depot

4.5/5(15 area reviews)

If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

Chester Depot
Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common, Chester, VT
The price is AED 584 per night from Aug 3 to Aug 4
AED 584
AED 637 total
3 Aug - 4 Aug
includes taxes & fees
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (369 reviews)
"It’s not like anyplace I have stayed before. It’s so homey and very comfortable. The staff is very friendly and it’s clean as a whistle."

Reviewed on 25 July 2025

Fullerton Inn
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

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 February 2025

Get rates
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AED 1,649 per night from Aug 17 to Aug 18
AED 1,649
AED 1,976 total
17 Aug - 18 Aug
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! (528 reviews)
"Really enjoyed our stay."

Reviewed on 18 July 2025

Woodstock Inn & Resort
See all 2,967 properties in Chester
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

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 February 2025

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
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! (45 reviews)
"Great spot! Close to food and entertainment. Great trails immediately outback. Had an issue with the lock and had ZeRo issues getting a hold of the management. They got a locksmith out and had it changed before we returned. Excellent response."

Reviewed on 21 July 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
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! (74 reviews)
"Nice, clean room in prime location"

Reviewed on 15 March 2025

Long Trail House at Stratton Mountain Resort
See all properties in Chester
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.

DaVallia Art & Accents

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.

Bonnie's Bundles Dolls