Photo by Elizabeth Massa Peroulakis

Search Resort Hotels in Chester

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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Chester Resorts

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Property grounds

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

10.0 out of 10, Exceptional, (1)
"We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Holiday Inn Club Vacations Oak 'n Spruce Resort
View from property

Holiday Inn Club Vacations Oak 'n Spruce Resort

2.0 star property
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Property grounds

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Mountain Lodge Apt!
Private kitchen

Mountain Lodge Apt!

Mountain Lodge Apt!
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
Pool

Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC

2.0 star property
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
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

The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is CA $348
CA $389 total
includes taxes & fees
Feb 14 - Feb 15
The Ponds at Foxhollow by Capital Vacations
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"The property is private. It’s the back half of the main house garage but it is well appointed and decorated. All one room. Nice kitchen and bath. Great stereo and TV. It was cold and snowing so we do no explore the trails on the property. "
The price is CA $217
CA $329 total
includes taxes & fees
Feb 2 - Feb 3
Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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 is Chester like for a resort vacation?
You deserve to get away, and a resort is the ideal place to find all the amenities and services you need for a relaxing stay in Chester. One of the comfortable resorts in the area might be just what you’re looking for, whether you’re hoping for great restaurants on site, a state-of-the-art fitness center, or activities for the kids.
What's the best resort for my stay in Chester?
Our highest-rated resort near Chester: Holiday Inn Club Vacations Oak ‘n Spruce Resort - Ski resort. 15 mi (24.1 km) from Chester. Enjoy the sauna, fitness center, and terrace.
What can I do in Chester?
Experience the local theater scene at Chester Town Hall, or bring the kids to Berkshire Scenic Railway Museum for some family fun. In the area, other attractions include Glendale Falls and Iroquis Waterfront.
What's the weather like in Chester?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What's the best way to get to and around Chester?
Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.