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.
Fullerton Inn
40 The Common Chester VT
The price is NT$4,389 per night from Jan 28 to Jan 29
NT$4,389
NT$4,784 total
Jan 28 - Jan 29
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! (410 reviews)
Great staff and service.
Reviewed on 2026/1/22
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is NT$9,757 per night from Feb 22 to Feb 23
NT$9,757
NT$12,122 total
Feb 22 - Feb 23
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! (561 reviews)
Excellent hotel, staff well trained.
Reviewed on 2026/1/21
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is NT$5,968 per night from Feb 22 to Feb 23
NT$5,968
NT$6,803 total
Feb 22 - Feb 23
includes taxes & fees
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (959 reviews)
Courteous and helpful staff
Reviewed on 2026/1/23
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.
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! (79 reviews)
Nice lodge. Room needs updating
Reviewed on 2025/10/19
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! (57 reviews)
ample room, close to ski lifts, pretty view, great renovations, sauna was great, family had a wonderful time!
Reviewed on 2025/12/22
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
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- Visit Central Vermont
- Visit Wilmington
- Visit Quechee
- Visit Gaysville
- Visit Killington
- Visit Arlington
- Fox Run Golf Course
- Visit Danby
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- Visit Grafton
- Visit Saxtons River
- Weston Playhouse
- Visit Dorset
- Visit Perkinsville
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- Mount Ascutney
- Jud Hartmann Gallery
- Visit North Pomfret
- Visit Stockbridge
- Ball Mountain Dam
- Visit Jacksonville
- Grafton Ponds Outdoor Center
- Visit Landgrove
- Gallery North Star
- Visit Taftsville
- Visit Norwich
- Okemo Mountain Resort
- Visit Brownsville
- Vermont Country Store
- Visit Mount Tabor
- Lowell Lake State Park
- Visit Manchester Center
- Green Mountain Sugar House
- Visit Manchester
- Baltimore Covered Bridge
- Visit Weston
- Visit Mendon
- Visit Rupert
- Dorsey Park
- Visit Rockingham
- Visit East Dorset
- Jamaica State Park
- Visit Cavendish
- Visit Ludlow
- Enterprise Rental Cars in Weston
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- Okemo Mountain Resort
- Killington Resort
- Bromley Mountain Ski Resort
- Mount Snow Golf Course
- Connecticut River
- Hildene
- Mount Ascutney
- Weston Playhouse
- American Express Ski Lift
- Vermont Country Store
- Historic Main Street
- Connecticut Lakes Region
- The Stone Church
- Bear Mountain Quad Ski Lift
- Emerald Lake State Park
