Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Chester
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is 8.378.854 ₫ per night from 19 Jan to 20 Jan
8.378.854 ₫
10.372.443 ₫ total
19 Jan - 20 Jan
includes taxes & fees
9.2/10 Wonderful! (560 reviews)
Luxurious and friendly resort! Loved it
Reviewed on 18 Dec 2025
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is 4.964.274 ₫ per night from 14 Jan to 15 Jan
4.964.274 ₫
5.659.272 ₫ total
14 Jan - 15 Jan
includes taxes & fees
8.8/10 Excellent! (951 reviews)
Clean, nice pool and hot tub, and good price!
Reviewed on 11 Jan 2026
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
The price is 4.432.847 ₫ per night from 26 Jan to 27 Jan
4.432.847 ₫
6.342.452 ₫ total
26 Jan - 27 Jan
includes taxes & fees
7.2/10 Good! (585 reviews)
Was surprised at the dirty floors in common area and in my room one of the curtain sheers was ripped, other curtains were hanging off hokks, caulking at sink looked old, cracked, carpets in staircase dirty. I fear this beautiful hotel is in a downward spiral. One front desk person directed me to ...
Reviewed on 9 Jan 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
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.
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.
