Best Resorts in Chester

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.

Our highest-rated resorts 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. Mountain Lodge Apt! - 17.2 mi (27.7 km) from Chester. Amenities include a fitness center.

Experience the local theater scene at Chester Town Hall, or bring the kids to Ashintully Gardens for some family fun. In the area, other attractions include Jacob’s Pillow and Otis Reservoir.

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.

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.