Chester Travel Guide

Tourist Guide

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Where to stay in Chester

Find the best Chester areas 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

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
The price is ₹14,055 per night from 29 Jun to 30 Jun
₹14,055
₹15,320 total
29 Jun - 30 Jun
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! (439 reviews)
"We had a wonderful weekend. Inn is a little dated but very cute. Room was clean and we sat out on our balcony with wine at night and coffee in the morning. Needed a dusting but comfortable. I would stay there again and recommend it to those traveling. Great location."

Reviewed on 21 Jun 2026

Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is ₹47,071 per night from 24 Jun to 25 Jun
₹47,071
₹55,929 total
24 Jun - 25 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! (586 reviews)
"If you're looking for a very comfortable stay in the quaint and historic town of Woodstock VT and don't worry about the expense, then the Woodstock Inn is the place for you!"

Reviewed on 16 Jun 2026

Woodstock Inn & Resort
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
The price is ₹12,157 per night from 29 Jun to 30 Jun
₹12,157
₹13,372 total
29 Jun - 30 Jun
includes taxes & fees
Stay at this hotel in Brattleboro. Enjoy free Wi-Fi, free parking and conference space. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (907 reviews)
"Love the historical aspects of this place."

Reviewed on 17 Jun 2026

Latchis Hotel
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.
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 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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
Stay at this ski aparthotel in Stratton. Enjoy free Wi-Fi, free parking and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager Ski Lift ...
8.6/10 Excellent! (83 reviews)
"Great location - the room was very clean and spacious. You don't check in at the property but at another one nearby. Hot tub was nicely maintained"

Reviewed on 31 Jan 2026

Long Trail House at Stratton Mountain Resort
Okemo Mountain Lodging  by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
77 Okemo Ridge Rd Ludlow VT
Stay at this holiday home in Ludlow. Enjoy free parking, laundry facilities and cable TV channels. Popular attractions Okemo Mountain Resort and Skywalker Carpet ...
7.8/10 Good! (28 reviews)
"Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband ..."

Reviewed on 26 Jun 2025

Okemo Mountain Lodging by Vail Resorts
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

Cities near Chester