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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.

Finding Chester Hotels

Chester is a good place to explore, but if it's hard to find accommodation and you're looking for more choices, these towns close by may have more of what you like.

  • 3 hotels in Middlefield
  • 5 hotels in Huntington
  • 39 hotels in Becket

Exploring Chester

The city of Chester has some interesting things to see and do. Popular attractions in and around Chester include:

  • Chester Town Hall
  • Pyramid Lake
  • Jacob's Pillow
  • Otis Ridge
  • Chesterfield Gorge
  • Otis Reservoir
  • October Mountain State Forest

When arranging your Chester getaway, you can also use ebookers to look for a convenient flight into Westfield, MA (BAF-Barnes Municipal) Airport. You can narrow down your search by number of stops, airline or time of departure to find the one that'll meet your needs.

When is the Best Time to Explore Chester?

If you're wondering when is the best time of year to visit Chester, you might find this info about seasonal weather useful when you are planning your trip. The warmest months in Chester are typically July and August, whereas the coldest months are usually January and February. The months with the most rain are July and August, whereas January and November have the least.

Here's an overview on how much rain you can expect and what the temperatures are going to be like:

  • From January to March, the average daytime temperature is 5°C and at night it is -8°C. Seasonal average rainfall is 305 mm.
  • If you visit between April and June, you can expect an average temp of 23°C during the day and 3°C at night. Average rainfall during this season is 398 mm.
  • The daytime average temp from July to September is 26°C and the night-time average is 12°C. Average precipitation for this season is 465 mm.
  • Between October and December, the average temp during the day is 15°C and -4°C at night. Seasonal average rain is 398 mm.
  • The average annual rainfall in Chester is 1566 mm.

Chester hotels essential information

Accommodation
785 hotels
Lowest Price
€92
Highest Price
€222
Popular hotels
D. Hotel Suites & Spa, Red Roof Inn PLUS+ West Springfield, Quality Inn West Springfield, La Quinta Inn & Suites by Wyndham Springfield MA, Life House Berkshires, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham, Tru by Hilton Chicopee Springfield, The Black Swan Lee - Lenox, Ascend Hotel Collection, The Ellery, Homewood Suites by Hilton Holyoke-Springfield/North, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Homewood Suites by Hilton Hadley Amherst, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, The Constance, The Whitlock, & The Dewey By The Lenox Collection