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 AED 584 per night from Oct 21 to Oct 22
AED 584
AED 637 total
21 Oct - 22 Oct
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! (371 reviews)
Great Inn in a quaint town.
"A wonderful little Inn with such a pleasant owner and just a great vibe there. Would absolutely recommend for a summer or winter stay. Can imagine it is beautiful in the winter."
Reviewed on 3 August 2025
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! (822 reviews)
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Reviewed on 17 September 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is AED 2,200 per night from Sep 21 to Sep 22
AED 2,200
AED 2,582 total
21 Sep - 22 Sep
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! (533 reviews)
Old world charm
"What a wonderful inn. Same class as The Greenbrier and The Homestead. Old world charm."
Reviewed on 12 September 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 24 February 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 13 August 2025
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Londonderry
Stay at this cabin in Londonderry. Enjoy free WiFi, a sauna, and balconies. Popular attractions Magic Mountain Ski Resort and Stratton Mountain Golf Course are ...
10/10 Exceptional! (4 reviews)
Beautiful property
"Had a wonderful time - brought my 5 year old daughter for a weekend and we absolutely enjoyed it."
Reviewed on 3 June 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
- DaVallia Art & Accents
- Bonnie's Bundles Dolls
- Killington Resort
- Okemo Mountain Resort
- Stratton Mountain Resort
- Mount Snow
- Green Mountain National Forest
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Keene State College
- Golf Club at Equinox
- Vermont Country Store
- Connecticut River
- Mount Ascutney
- Equinox Preservation Trust
- Stratton Mountain Summit Gondola
- Billings Farm and Museum
- Hildene
- Mount Snow Golf Course
- Landmark College
- Manchester Designer Outlets
- Connecticut Lakes Region
- Mt Ascutney State Park
- American Express Ski Lift
- Historic Main Street
- Spofford Lake
- Blow-Me-Down Bridge
- Emerald Lake State Park
- Lake Rescue
- Colonial Theatre
- Sunrise Village Triple Ski Lift
- Molly Stark State Park
