Chester Travel Guide

Tourist Guide

A covered wooden bridge over a river, surrounded by rocky terrain and greenery.
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, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
The price is ₹12,115 per night from 3 Dec to 4 Dec
₹12,115
₹13,205 total
3 Dec - 4 Dec
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 ...
Fullerton Inn
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
698 VT-11 Chester VT
The price is ₹16,282 per night from 1 Dec to 2 Dec
₹16,282
₹17,747 total
1 Dec - 2 Dec
includes taxes & fees
Stay at this B&B in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
9.2/10 Wonderful! (130 reviews)
"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 ..."

Reviewed on 8 Oct 2026

Stone Hearth Inn and Eatery
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is ₹31,082 per night from 30 Nov to 1 Dec
₹31,082
₹38,347 total
30 Nov - 1 Dec
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! (629 reviews)
"Fantastic stay at Woodstock Inn this week! The room and property were spotless, and the staff was incredibly kind and welcoming. The spa was beautiful, the food at Red Rooster was excellent, and the athletic center, pool, and hot tub were all great. The entire property has a quiet, peaceful atmosphere ..."

Reviewed on 6 Nov 2026

Woodstock Inn & Resort
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! (70 reviews)
"It is a wonderful place to stay at any time for coming foliage or ski. The location is excellent, quiet and very clean inside. We felt like at home, We will stay again when we visit woodstook area next time."

Reviewed on 15 Oct 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! (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."

Reviewed on 11 Oct 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 Galaxy Bowl ...
7.6/10 Good! (31 reviews)
"Don’t ever rent at this place for the condo rentals they sent us to the wrong address, I could not get in contact with the so-called property manager for over an hour or more. We had no toilet paper, we had no hairdryer, no paper towels, we didn’t even know where the keys were or shampoo or soap. ..."

Reviewed on 15 Oct 2026

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.

Stay near popular Chester attractions

Cities near Chester