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
$129 nightly
The price is $141 total per night from May 24 to May 25
$141 total
May 24 - May 25
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! (434 reviews)
Fun stay at a neat old inn in a very convenient and lovely location, walking distance to good food and shopping. This is an older hotel that doesn’t have all the updated and most modern conveniences but if it did, it would be twice as expensive and I probably would not have stayed there. And it would ...
Reviewed on May 10, 2026
Historic 150-year-old farmhouse, Jacuzzi included
Chester VT
$382 nightly
The price is $427 total per night from May 17 to May 18
$427 total
May 17 - May 18
Total with taxes and fees
Stay at this farm stay in Chester. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions DaVallia Art & Accents and Bonnie's Bundles ...
9.8/10 Exceptional! (16 reviews)
We had a great (but short!) stay at the Farmhouse. We used this as our base to tour colleges in the greater area, and we wish we had more time to enjoy the home. It was great to be able to soak in the hot tub, cook dinner, and relax after days of walking and driving.The home had lots of charm, and ...
Reviewed on Apr 2, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from May 25 to May 26
$395 total
May 25 - May 26
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! (577 reviews)
Everything was excellent
Reviewed on May 5, 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
Mountainside 5-BR Ski-In/Out Okemo Villa
Ludlow VT
Stay at this vacation home in Ludlow. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and Quantum Ski Lift ...
9.8/10 Exceptional! (6 reviews)
Fantastic Ski in Ski out location
Amazing house
Reviewed on Feb 24, 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.
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- DaVallia Art & Accents
- Bonnie's Bundles Dolls
- Stratton Mountain Resort
- Mount Snow
- Okemo Mountain Resort
- Killington Resort
- Green Mountain National Forest
- Bromley Mountain Ski Resort
- Magic Mountain Ski Resort
- Billings Farm and Museum
- Keene State College
- Hildene
- Golf Club at Equinox
- Landmark College
- Equinox Preservation Trust
- Spofford Lake
- Battenkill River
- Vermont Country Store
- The Stone Church
- Connecticut River
- Weston Playhouse
- Manchester Designer Outlets
- Mount Snow Golf Course
- Historic Main Street
- Emerald Lake State Park
- Sunrise Village Triple Ski Lift
- Mt Ascutney State Park
- Marsh-Billings-Rockefeller National Historical Park
