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, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is SAR 1,273 per night from Dec 16 to Dec 17
SAR 1,273
SAR 1,565 total
16 Dec - 17 Dec
includes taxes & fees
Book a stay at this 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! (552 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town
Reviewed on 26 November 2025
The Shire Woodstock
46 Pleasant St. Woodstock VT
The price is SAR 433 per night from Dec 10 to Dec 11
SAR 433
SAR 505 total
10 Dec - 11 Dec
includes taxes & fees
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (884 reviews)
Clean good service and location
Reviewed on 22 November 2025
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
The price is SAR 597 per night from Dec 7 to Dec 8
SAR 597
SAR 802 total
7 Dec - 8 Dec
includes taxes & fees
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (815 reviews)
Staff was great. Our room was okay… broken blinds and lots of scuffs on walls
Reviewed on 16 November 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 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! (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
Long Trail House at Stratton Mountain Resort
761 Stratton Access Rd Stratton VT
Book a stay at this ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.4/10 Very Good! (77 reviews)
Nice lodge. Room needs updating
Reviewed on 19 October 2025
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 Pico Mountain at Killington ...
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 October 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
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.
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.
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
- Bonnie's Bundles Dolls
- DaVallia Art & Accents
- Stratton Mountain Resort
- Mount Snow
- Okemo Mountain Resort
- Killington Resort
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Green Mountain National Forest
- Keene State College
- Mount Ascutney
- Mount Snow Golf Course
- Hildene
- Stratton Mountain Summit Gondola
- Connecticut River
- Vermont Country Store
- American Express Ski Lift
- Billings Farm and Museum
- Sunrise Village Triple Ski Lift
- Weston Playhouse
- Golf Club at Equinox
- Landmark College
- Manchester Designer Outlets
- Equinox Preservation Trust
- Blow-Me-Down Bridge
- The Stone Church
- Historic Main Street
- Connecticut Lakes Region
- Viking Nordic Center
- Woodstock Town Hall Theatre
- Spofford Lake
- Bear Mountain Quad Ski Lift
