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 SAR 484 per night from Apr 1 to Apr 2
SAR 484
SAR 527 total
includes taxes & fees
1 Apr - 2 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! (332 reviews)
"Great property!"
Reviewed on 4 March 2025
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road, Brownsville, VT
The price is SAR 446 per night from Apr 6 to Apr 7
SAR 446
SAR 538 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! (681 reviews)
"Very nice and easy stay"
Reviewed on 27 March 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is SAR 1,122 per night from Apr 6 to Apr 7
SAR 1,122
SAR 1,399 total
includes taxes & fees
6 Apr - 7 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! (506 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
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! (41 reviews)
"very clean and easy to access close to mountain"
Reviewed on 24 December 2024
Long Trail House at Stratton Mountain Resort
761 Stratton Access Rd, Stratton, VT
Stay at this 3-star ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.4/10 Very Good! (74 reviews)
"Nice, clean room in prime location"
Reviewed on 15 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
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
- Okemo Mountain Resort
- Killington Resort
- Mount Snow
- Bromley Mountain Ski Resort
- Green Mountain National Forest
- Magic Mountain Ski Resort
- Keene State College
- Golf Club at Equinox
- Connecticut River
- Hildene
- Blow-Me-Down Bridge
- Mount Ascutney
- Manchester Designer Outlets
- Mount Snow Golf Course
- Equinox Preservation Trust
- Vermont Country Store
- American Express Ski Lift
- Stratton Mountain Summit Gondola
- Landmark College
- Billings Farm and Museum
- Connecticut Lakes Region
- Spofford Lake
- Sunrise Village Triple Ski Lift
- The Stone Church
- Colonial Theatre
- Vermont Summer Festival
- Mt Ascutney State Park
- Battenkill River
- Historic Main Street