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
$129 nightly
The price is $141 total per night from Mar 1 to Mar 2
$141 total
Mar 1 - Mar 2
Total with taxes and 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! (414 reviews)
The staff was great from the minute we checked in to the great service we received at the tavern
Reviewed on Feb 8, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$142 nightly
The price is $154 total per night from Mar 2 to Mar 3
$154 total
Mar 2 - Mar 3
Total with taxes and 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! (975 reviews)
Nice & helpful staff, great location, clean
Reviewed on Feb 10, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night from Feb 22 to Feb 23
$384 total
Feb 22 - Feb 23
Total with taxes and 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! (562 reviews)
Excellent hotel, staff well trained.
Reviewed on Jan 21, 2026
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 VT
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 Feb 24, 2025
Riverfront, family fun, amazing rec room, close to Magic & Okemo
Chester VT
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bonnie's Bundles Dolls and ...
9.8/10 Exceptional! (13 reviews)
Clean, spacious, and well-equipped home that was a perfect fit for a ski weekend for our family of 6. The kids loved the turf play area and all the games!
Reviewed on Jan 24, 2026
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! (83 reviews)
Great location - the room was very clean and spacious. You don't check in at the property but at another one nearby. Hot tub was nicely maintained
Reviewed on Jan 31, 2026
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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- Bonnie's Bundles Dolls
- DaVallia Art & Accents
- Stratton Mountain Resort
- Okemo Mountain Resort
- Mount Snow
- Killington Resort
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Green Mountain National Forest
- Keene State College
- Golf Club at Equinox
- Connecticut River
- Landmark College
- Hildene
- Sunrise Village Triple Ski Lift
- Manchester Designer Outlets
- Billings Farm and Museum
- Vermont Country Store
- Mount Snow Golf Course
- Stratton Mountain Summit Gondola
- American Express Ski Lift
- Emerald Lake State Park
- Spofford Lake
- Weston Playhouse
- Stratton Mountain Golf Course
- Colonial Theatre
- The Stone Church
- Claremont Opera House
- Equinox Preservation Trust
- The Putney School