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, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.
Fullerton Inn
40 The Common Chester VT
The price is CA $184 per night from Nov 9 to Nov 10
CA $184
CA $200 total
Nov 9 - Nov 10
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 ...
Stone Hearth Inn and Eatery
698 VT-11 Chester VT
The price is CA $342 per night from Oct 26 to Oct 27
CA $342
CA $373 total
Oct 26 - Oct 27
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! (130 reviews)
"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 ..."
Reviewed on Oct 8, 2026
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
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 ...
9/10 Wonderful! (69 reviews)
"Property was good. We founded a lot of cobble webs around the house. The stove was dirty when we used and made a horrible smell of burned. The guys next door were very loud at 3am and we couldn't sleep till they left around 5-6am. Will for sure be back if we have a chance. The place is well located ..."
Reviewed on Oct 5, 2026
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Ludlow VT
Book a stay at this family-friendly vacation home in Ludlow. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and ...
9.6/10 Exceptional! (146 reviews)
"Great cabin in the pines. Host very communicative and answered all our questions with good response time. Property was clean and well maintained. Definitely would book this one again!"
Reviewed on Sep 25, 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.
