Chester
Travel Guide
Visit Chester
Where to stay in Chester
Find the best Chester areas and neighborhoods for the activities you enjoy most.
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
The price is CA $194 per night from Jun 9 to Jun 10
CA $194
CA $211 total
Jun 9 - Jun 10
includes taxes & 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! (435 reviews)
"Very nice older Inn with on-site tavern in a classic Vermont town. Quite and comfortable stay."
Reviewed on May 22, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is CA $598 per night from Jun 9 to Jun 10
CA $598
CA $719 total
Jun 9 - Jun 10
includes taxes & 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! (582 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
Reviewed on May 22, 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
The price is CA $231 per night from Jun 14 to Jun 15
CA $231
CA $313 total
Jun 14 - Jun 15
includes taxes & fees
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (848 reviews)
"dirty room and overcapacity. No breakfast"
Reviewed on Jun 2, 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
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Ludlow VT
Book a stay at this family-friendly cabin in Ludlow. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Okemo Mountain Resort and Sunshine ...
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.
