Chester
Travel Guide
Visit Chester
Where to stay in 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
The price is €121 per night from 28 May to 29 May
€121
28 May - 29 May
includes taxes & fees
Stay at this inn in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their 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 22 May 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is €509 per night from 17 Jun to 18 Jun
€509
17 Jun - 18 Jun
includes taxes & fees
Stay at this luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (580 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
Reviewed on 22 May 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is €166 per night from 8 Jun to 9 Jun
€166
8 Jun - 9 Jun
includes taxes & fees
Stay at this spa hotel in Cavendish. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (1,000 reviews)
"Hotel is not near any resturants and it had no on-premisis restaurant for breakfast."
Reviewed on 17 May 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 Wi-Fi, an in-room coffee maker 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 11 Mar 2026
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3387 East Mountain Road Killington VT
Stay at this ski cabin in Killington. Enjoy free Wi-Fi, free parking and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I ...
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 10 May 2026
Mountainside 5-BR Ski-In/Out Okemo Villa
Ludlow VT
Stay at this holiday home in Ludlow. Enjoy a fitness centre, 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 24 Feb 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.
Things to do
Colonial Flintlock Musket Experience
€110
per adult
100% of travellers recommend
