5/5 - Excellent
Verified traveler
Very friendly area and quaint!
Chester, VT
Travel Guide
Visit Chester
Where to stay in Chester
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.
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! (829 reviews)
"Great little motel. Clean, well appointed, friendly staff and walkable location. We did not have good weather, but great fire pits and chairs near river."
Reviewed on Sep 25, 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is ￥80,575 per night from Oct 26 to Oct 27
￥80,575
￥95,211 total
Oct 26 - Oct 27
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! (534 reviews)
"Clean room. Staff very polite and helpful"
Reviewed on Sep 24, 2025
The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
The price is ￥22,227 per night from Sep 28 to Sep 29
￥22,227
￥32,662 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
7.2/10 Good! (533 reviews)
"Such a beautiful location! Especially love the fire pit outside of the Falcon Bar"
Reviewed on Sep 24, 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 Feb 24, 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! (49 reviews)
"Great value, comfortable space, responsive host!"
Reviewed on Aug 13, 2025
Winterplace at Okemo
77 Okemo Ridge Rd, Ludlow, VT
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars ...
8.6/10 Excellent! (24 reviews)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place"
Reviewed on Sep 15, 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.
Reviews of Chester
4.2
Top Destination
4/5 - Good
Verified traveler
Quaint and beautiful town with good representation of Vermont.
4/5 - Good
Verified traveler
Cute, quiet little town.
5/5 - Excellent
BL
Chester is a cute little town. We went to ski at Okemo and this was the last place available, so we stumbled onto this property. Glad we did, going out to eat was much easier than in Ludlow and everyone we met couldn't be nicer.
4/5 - Good
Verified traveler
The Scottish Inn Pub was excellent!
3/5 - Okay
Verified traveler
Not much to it
