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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct

Browse Select Chester Resorts

Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (531)
"Relaxing "
The price is 10.762.017 ₫
12.995.990 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Woodstock Inn & Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (732)
"Great place great scenery amazing staff"
The price is 2.963.896 ₫
3.589.356 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Black Bear Lodge at Stratton Mountain Resort
Indoor spa tub

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
7.6 out of 10, Good, (911)
"Nice area"
The price is 3.920.637 ₫
4.743.971 ₫ total
includes taxes & fees
24 Aug - 25 Aug
The Black Bear Lodge at Stratton Mountain Resort
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.6 out of 10, Excellent, (215)
"Very nice being right on the mountain. "
The price is 3.660.283 ₫
4.380.501 ₫ total
includes taxes & fees
10 Sept - 11 Sept
Mount Snow Grand Summit Resort
Equinox Resort Residences
Lobby sitting area

Equinox Resort Residences

4.5 star property
8.0 out of 10, Very good, (2)
"The setting is beautiful. The staff were amazing - kind and attentive. Our room was very dated and in need of updating including the bathrooms. The furniture in the room was an odd collection of pieces that could have come from a yard sale. It was not up to the standard we expected given the cost of the room and the overall resort vibe. "
The price is 26.031.470 ₫
36.837.759 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Equinox Resort Residences
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.
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Top Chester Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"."
Murray 1-night trip
Posted 2 days ago
The Shire Woodstock

Frequently asked questions

What can I expect from a resort holiday in Chester?
You deserve to get away, and a resort is the perfect place to indulge in all the amenities and services you need for a relaxing trip to Chester. One of the comfortable resorts in the surrounding area could be just what you're looking for, whether you want a luxurious suite, blissful spa treatments or nightly entertainment options.
What can I do in Chester?
Travellers enjoy the skiing and other winter sports in Chester, and have good things to say about activities such as shopping. DaVallia Art & Accents and Bonnie's Bundles Dolls are a few of the interesting sights to visit. In the area, other attractions include Vermont Country Store and Plummer's Sugar House.
What's the seasonal weather like in Chester?
The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What's the best way to get to and around Chester?
Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) from the city centre. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.