The Best Chester, VT Resorts from CNY1,051

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Compare 36 Resorts in Chester with updated reviews, rates, and availability.

Other property types in Chester

"My husband and I loved this little cottage , we will definitely be back."

"Will be back!!"

Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"

$384 total

includes taxes & fees

16 Jun - 17 Jun

Chester Resorts information

Number of reviews	2,045
Accommodation	36 Resorts
Lowest Price	CNY1,051
Highest Price	CNY2,892

Frequently asked questions

What can I expect from a resort vacation in Chester?

You deserve to get away, and a resort is the perfect place to treat yourself to the amenities and services you need for a relaxing trip to Chester. One of the comfortable resort hotels in the surrounding area might be just what you’re looking for, whether you want a luxurious suite, shopping possibilities, or fun activities to try.

What's a top resort in Chester?

Here are our top-rated resorts around Chester: Woodstock Inn & Resort - Luxury resort. 25.2 mi (40.5 km) from Chester. Features 4 restaurants, 2 bars, and a golf course. The Black Bear Lodge at Stratton Mountain Resort - Ski resort, 5-minute walk from Stratton Mountain Resort. 18.7 mi (30.1 km) from Chester. Has 10 restaurants, 2 bars, and a full-service spa. Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel - 15.4 mi (24.7 km) from Chester. Enjoy the seasonal outdoor pool, bar, and an indoor pool. Mount Snow Grand Summit Resort - Ski resort, 5-minute walk from Mount Snow. 25.5 mi (41 km) from Chester. Amenities include ski-in/ski-out access, a full-service spa, and a fitness center. Equinox Resort Residences - Luxury resort. 25 mi (40.3 km) from Chester. Access to 4 restaurants, 2 bars, and a golf course.

What can I do in Chester?

Travelers 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 Baltimore Covered Bridge.

What's the weather like in Chester?

The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches 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) away from the city center. You can also search 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, consider renting a car to take in more sights.