Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Chester
The Shire Woodstock
46 Pleasant St., Woodstock, VT
8.6/10 Excellent! (824 reviews)
Best Hotel on our Vermont Trip
"Excellent all around. Loved the room, so comfortable and well furnished and, of course, the balcony looking over the river. Easy check-in and they accommodated my request fro a ground floor room. Parking right outside your room which helps a lot when you have a ton of luggage. We don't travel ..."
Reviewed on 21 Sept 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is 19.784.086 ₫ per night from 22 Oct to 23 Oct
19.784.086 ₫
22.924.711 ₫ total
22 Oct - 23 Oct
includes taxes & fees
9.2/10 Wonderful! (533 reviews)
Old world charm
"What a wonderful inn. Same class as The Greenbrier and The Homestead. Old world charm."
Reviewed on 12 Sept 2025
The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is 2.939.878 ₫ per night from 28 Sept to 29 Sept
2.939.878 ₫
4.641.658 ₫ total
28 Sept - 29 Sept
includes taxes & fees
7.2/10 Good! (531 reviews)
"The hotel prominently promotes walking trails in and near on their property. While they provide maps no staff could explain how to access. The maps were very confusing. We set out and could not find a trail head. We finally used Google Maps and found that the nearest access was a few blocks away ..."
Reviewed on 14 Sept 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.
