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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 Cheshire Hotels

Cheshire is a good place to check out, 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're looking for.

  • 21 hotels in Lanesborough
  • 2 hotels in New Ashford
  • 5 hotels in Adams

Top Hotels and Other Accommodation Options in Cheshire

When you're deciding where to stay in Cheshire, you can easily and quickly search ebookers for hotels that offer services such as high-speed Internet, free airport transport or a swimming pool. You can use the filters to narrow down your search for a hotel, so you can get the services that are important to you, such as air conditioning or an in-room kitchen.

Guests like this hotel in Cheshire for the free breakfast:

  • Harbour House Inn

Exploring Cheshire

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

  • Mount Greylock State Reservation
  • St Mary's of the Assumption Church
  • Mount Greylock State Reservation Visitor Center
  • Mount Greylock
  • Brodie Mountain
  • Jiminy Peak Mountain Resort
  • Williamstown Theatre Festival

When making plans for your trip to Cheshire, you can also use ebookers to find a convenient flight into Pittsfield, MA (PSF-Pittsfield 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 Cheshire?

If you're wondering when is the best time of year to explore Cheshire, you might find this info about seasonal weather useful when you are planning your trip. The warmest months in Cheshire 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 3°C and at night it is -10°C. Seasonal average rainfall is 283 mm.
  • If you visit between April and June, you can expect an average temp of 21°C during the day and 1°C at night. Average rainfall during this season is 388 mm.
  • The daytime average temp from July to September is 25°C and the night-time average is 10°C. Average precipitation for this season is 438 mm.
  • Between October and December, the average temp during the day is 13°C and -6°C at night. Seasonal average rain is 376 mm.
  • The annual rainfall average in Cheshire is 1484 mm.

Cheshire hotels essential information

Accommodation
892 hotels
Lowest Price
€81
Highest Price
€204
Popular hotels
The Red Lion Inn, Life House Berkshires, The Yankee, Trademark Collection by Wyndham, The Black Swan Lee - Lenox, Ascend Hotel Collection, Hotel Downstreet, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Vacation Village in the Berkshires, The Constance, The Whitlock, & The Dewey By The Lenox Collection, The Williams Inn, FairBridge Inn Express, Hampton Inn & Suites Berkshires-Lenox, Quality Inn, Berkshire Mountain Lodge, Hotel On North

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