Search Resorts in Chester

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Featured Resorts in Chester

Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (490)
"The garden level hallways needs a facelift. Room was fine but the corridor carpet had stains and it looked a little dingy. Expected more for a 5 star resort."
The price is P17,584
P21,930 total
includes taxes & fees
Jan 20 - Jan 21, 2025
Woodstock Inn & Resort
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, (878)
"Very nice, clean property. A tad bit outdated but for a value in the area it’s well worth it. We had an enjoyable stay. "
The price is P10,527
P12,738 total
includes taxes & fees
Jan 20 - Jan 21, 2025
The Black Bear Lodge at Stratton Mountain Resort
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (170)
"👍"
The price is P16,472
P19,713 total
includes taxes & fees
Jan 22 - Jan 23, 2025
Mount Snow Grand Summit Resort
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (651)
"Don't have elevator, and no hot breakfast provided "
The price is P8,763
P10,353 total
includes taxes & fees
Jan 20 - Jan 21, 2025
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel
Equinox Resort Residences
Indoor pool, open 8:00 AM to 6:00 PM, sun loungers

Equinox Resort Residences

4.5 star property
8.0 out of 10, Very Good, (2)
"3 room townhouse was great . Check in time is 4 . Wasn’t ready till 430 Also I think carpets in house need to be washed Other than that everything was 10 . "
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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Other property types in Chester

Long Trail House at Stratton Mountain Resort
Pool

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is P22,292
P27,709 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Long Trail House at Stratton Mountain Resort
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (40)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
The price is P29,640
P40,367 total
includes taxes & fees
Jan 10 - Jan 11, 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.

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 sauna. Mount Snow Grand Summit Resort - Ski resort, 5-minute walk from Mount Snow. 25.5 mi (41 km) from Chester. Enjoy the ski-in/ski-out access, spa, and fitness center. Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel - 15.4 mi (24.7 km) from Chester. Amenities include a seasonal outdoor pool, a bar, and an indoor pool. 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. Vermont Country Store offers fun for the whole family, while Okemo Mountain Resort is one of the most popular places to visit nearby. A few other attractions you may want to see are DaVallia Art & Accents and Bonnie’s Bundles Dolls.
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.