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Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Chester?
Use Expedia to help you arrange a flight to Westfield, MA (BAF-Barnes Municipal) airport or Pittsfield, MA (PSF-Pittsfield Municipal) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are an important consideration when you plan a trip, so we make it easy to get what you'd like to make your stay relaxing and comfortable. If you want a posh hotel with fine dining, a spa, or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Chester has to offer. Chester has some interesting things to see and do including Chester Town Hall, so you might want to take in the local sights during your visit.
When can I expect good weather in Chester?
Planning for the weather is a good way to make your trip to Chester relaxing and enjoyable, especially when you're splurging. 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 there to see and do in Chester?
Experience Chester with a stop at Chester Town Hall, Glendale Falls, and Pyramid Lake. If you have spare time during your trip, you might want to make a stop at Jacob's Pillow and Otis Ridge.