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.
Fullerton Inn
40 The Common, Chester, VT
The price is AED 474 per night from Apr 12 to Apr 13
AED 474
AED 516 total
includes taxes & fees
12 Apr - 13 Apr
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! (344 reviews)
"Excellent service to help resolve reservation mix up. Small but serviceable room. Very limited breakfast. On premises restaurant was excellent for dinner"
Reviewed on 22 March 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is AED 1,098 per night from Apr 14 to Apr 15
AED 1,098
AED 1,370 total
includes taxes & fees
14 Apr - 15 Apr
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! (507 reviews)
Wonderful friendly staff and great environment
"All the staff, whether the bartender, wait staff, men at the front door, desk clerk everyone greeting my wife and I with a smile and were very helpful."
Reviewed on 29 March 2025
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road, Brownsville, VT
The price is AED 437 per night from Apr 6 to Apr 7
AED 437
AED 526 total
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (682 reviews)
"Wish they had a phone signal."
Reviewed on 2 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.
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! (22 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 Pico Mountain at Killington ...
9/10 Wonderful! (42 reviews)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient."
Reviewed on 28 March 2025
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Mount Holly
Stay at this cabin in Mount Holly. Enjoy free WiFi, a garden, and patios. Popular attractions Okemo Mountain Resort and Lake Ninevah are located nearby.
9.8/10 Exceptional! (198 reviews)
Amazing
"Location was perfect. Cabin cute and comfortable. Pond was an amazing bonus with lots of cool birds. We had the best vacation there ever!"
Reviewed on 29 March 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
- Bromley Mountain Ski Resort
- Keene State College
- Green Mountain National Forest
- Magic Mountain Ski Resort
- Stratton Mountain Summit Gondola
- Connecticut River
- Golf Club at Equinox
- Blow-Me-Down Bridge
- Equinox Preservation Trust
- Mount Ascutney
- Hildene
- Manchester Designer Outlets
- Vermont Country Store
- Mount Snow Golf Course
- Landmark College
- Billings Farm and Museum
- American Express Ski Lift
- Spofford Lake
- Connecticut Lakes Region
- Colonial Theatre
- Vermont Summer Festival
- The Stone Church
- Emerald Lake State Park
- Saint-Gaudens National Historic Site
- Marsh-Billings-Rockefeller National Historical Park
- Mt Ascutney State Park