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 SAR 559 per night from Jun 30 to Jul 1
SAR 559
SAR 609 total
30 Jun - 1 Jul
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! (362 reviews)
"Very cute hotel, friendly staff, charming location. The bed was a little saggy, but otherwise my room was great."
Reviewed on 21 June 2025
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
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is SAR 1,609 per night from Jul 6 to Jul 7
SAR 1,609
SAR 1,935 total
6 Jul - 7 Jul
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! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."
Reviewed on 20 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.
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
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Andover
Book a stay at this family-friendly vacation home in Ludlow. Enjoy a garden, laundry facilities, and patios. Popular attractions Mill Museum and Weston Playhouse ...
8.8/10 Excellent! (18 reviews)
Ski weekend
"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too!"
Reviewed on 30 December 2024
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! (43 reviews)
"Very nice place only negative was the sauna did not work"
Reviewed on 28 April 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
- Stratton Mountain Resort
- Okemo Mountain Resort
- Mount Snow
- Killington Resort
- Green Mountain National Forest
- Bromley Mountain Ski Resort
- Keene State College
- Magic Mountain Ski Resort
- Connecticut River
- Golf Club at Equinox
- Stratton Mountain Summit Gondola
- Hildene
- Mount Ascutney
- Vermont Country Store
- Billings Farm and Museum
- Equinox Preservation Trust
- Connecticut Lakes Region
- Mt Ascutney State Park
- American Express Ski Lift
- Vermont Summer Festival
- Mount Snow Golf Course
- Historic Main Street
- Manchester Designer Outlets
- Landmark College
- Spofford Lake
- Blow-Me-Down Bridge
- Saint-Gaudens National Historic Site
- Battenkill River
- Cornish-Windsor Covered Bridge
- Emerald Lake State Park