Chester

Travel Guide

Where to stay in Chester

Default Image

Chester Depot

If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

Chester Depot
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (832 reviews)
"Nice view but no balcony. Internet good"

Reviewed on 1 Oct 2025

The Shire Woodstock
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is €421 per night from 2 Nov to 3 Nov
€421
2 Nov - 3 Nov
includes taxes & fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (534 reviews)
"Clean room. Staff very polite and helpful"

Reviewed on 24 Sept 2025

Woodstock Inn & Resort
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is €285 per night from 13 Oct to 14 Oct
€285
13 Oct - 14 Oct
includes taxes & fees
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
7.2/10 Good! (539 reviews)
Beautiful
"Beautiful room, clean, and several amenities."

Reviewed on 29 Sept 2025

The Equinox Golf Resort & Spa
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

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester
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! (23 reviews)
Hidden gem!
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"

Reviewed on 24 Feb 2025

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
3387 East Mountain Road, Killington, VT
Stay at this 3-star ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage ...
9/10 Wonderful! (49 reviews)
"Great value, comfortable space, responsive host!"

Reviewed on 13 Aug 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend, VT
Stay at this lodge in Townshend. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Townshend State Park and Moore Free Library are located ...
"My family and I had the most wonderful stay at this beautiful Townshend, VT home! It was not only spotless and cozy, but also perfectly pet-friendly—Julie truly thought of everything. Both our family’s and our pet’s needs were taken care of, which made the experience even more special.Julie’s communication ..."

Reviewed on 21 Sept 2025

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
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