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
The price is ₩332,984 per night from Sep 16 to Sep 17
₩332,984
₩388,259 total
Sep 16 - Sep 17
includes taxes & fees
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! (817 reviews)
"great location and the staff were great"
Reviewed on Sep 10, 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is ₩834,802 per night from Sep 21 to Sep 22
₩834,802
₩979,603 total
Sep 21 - Sep 22
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! (532 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."
Reviewed on Jul 30, 2025
The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
The price is ₩197,814 per night from Sep 17 to Sep 18
₩197,814
₩293,753 total
Sep 17 - Sep 18
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! (525 reviews)
"Nothing additional to add"
Reviewed on Aug 28, 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.
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 ...
8.8/10 Excellent! (47 reviews)
"Great value, comfortable space, responsive host!"
Reviewed on Aug 13, 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! (74 reviews)
"Nice, clean room in prime location"
Reviewed on Mar 15, 2025
Solitude Village at Okemo
77 Okemo Ridge Rd, Ludlow, VT
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Snow Stars Carpet ...
8/10 Very Good! (27 reviews)
Very peaceful!!!
"Nice and quiet. Self contained in the building. Pool and hottub were great"
Reviewed on Sep 1, 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
