Chester, VT
Travel Guide
Visit Chester
Where to stay in Chester
Find the best Chester areas and neighborhoods for the activities you enjoy most. Learn more about Chester
Learn more about Chester
Chester Depot
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
$149 nightly
The price is $162 total per night from Jun 23 to Jun 24
$162 total
Jun 23 - Jun 24
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 ...
8.2/10 Very Good! (437 reviews)
"This property had a lot of history to tell. The owner was very friendly and accommodating. The room was clean and the bed was comfortable. The restaurant in the hotel was very good too."
Reviewed on Jun 14, 2026
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! (24 reviews)
"I had a great stay! Everything was as shown and described in the listing. My only advice is-if you are staying there during mud season make sure you have a AWD/4WD vehicle-the road to the property can get pretty bad."
Reviewed on Mar 11, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$509 nightly
The price is $560 total per night from Jun 28 to Jun 29
$560 total
Jun 28 - Jun 29
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. ...
9.4/10 Exceptional! (586 reviews)
"If you're looking for a very comfortable stay in the quaint and historic town of Woodstock VT and don't worry about the expense, then the Woodstock Inn is the place for you!"
Reviewed on Jun 16, 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! (24 reviews)
"I had a great stay! Everything was as shown and described in the listing. My only advice is-if you are staying there during mud season make sure you have a AWD/4WD vehicle-the road to the property can get pretty bad."
Reviewed on Mar 11, 2026
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3387 East Mountain Road Killington VT
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage ...
9/10 Wonderful! (62 reviews)
"Very quiet location secluded and peaceful. Location is not identified, no road sign or driveway entrance address. I booked within 3 days of check-in, instructions did not get emailed until after check in time, host did answer phone when called but email was received 30 minutes later. It's a unique ..."
Reviewed on May 10, 2026
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish VT
Stay at this cabin in Cavendish. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Phineas Gage Memorial and Mount Ascutney are located ...
10/10 Exceptional! (40 reviews)
"Beautiful location, very private, quiet. Cabins are new, beautiful and had all the amenities. Available outdoor hot tub, kayaks and paddle boards for use at nearby ponds. Highly recommend if you're looking for a camping-like experience in the woods of Vermont."
Reviewed on Jun 18, 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
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.
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- DaVallia Art & Accents
- Bonnie's Bundles Dolls
- Stratton Mountain Resort
- Killington Resort
- Mount Snow
- Okemo Mountain Resort
- Green Mountain National Forest
- Connecticut River
- Bromley Mountain Ski Resort
- Billings Farm and Museum
- Landmark College
- Golf Club at Equinox
- Hildene
- Emerald Lake State Park
- Magic Mountain Ski Resort
- Manchester Designer Outlets
- Vermont Country Store
- The Stone Church
- Keene State College
- Battenkill River
- Equinox Preservation Trust
- Spofford Lake
- Molly Stark State Park
- Historic Main Street
- Weston Playhouse
- Mount Snow Golf Course
- Madame Sherri Forest
- Mt Ascutney State Park
- Woodstock Town Hall Theatre