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, (483)
"Lovely hotel. Could do with some updates in areas but a very unique picturesque place . "
The price is P17,619
P21,973 total
includes taxes & fees
Dec 16 - Dec 17
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, (874)
"Pleasant staff and good location. dorm line feel to facility."
The price is P8,374
P10,132 total
includes taxes & fees
Nov 24 - Nov 25
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, (165)
"The staff were extremely friendly and helpful in the surrounding area. Tons of great food and shopping, and beautiful views - would absolutely recommend this place to stay in Vermont !"
The price is P9,658
P11,558 total
includes taxes & fees
Nov 24 - Nov 25
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, (649)
"Don't have elevator, and no hot breakfast provided "
The price is P5,986
P7,329 total
includes taxes & fees
Dec 3 - Dec 4
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

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, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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)
"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!"
The price is P19,313
P24,007 total
includes taxes & fees
Nov 24 - Nov 25
Long Trail House at Stratton Mountain 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.

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: 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. Features 10 restaurants, 2 bars, and a sauna. Woodstock Inn & Resort - Luxury resort. 25.2 mi (40.5 km) from Chester. Has 4 restaurants, 2 bars, and a golf course. 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. If you brought the kids, you can head to DaVallia Art & Accents or Bonnie’s Bundles Dolls for some family fun. Okemo Mountain Resort and Stratton Mountain Resort are a couple additional top attractions in the area.
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.