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Find hotels in Cheshire, MA from £61

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Top 10 Cheshire hotels and places to stay

More cheap stays in Cheshire

Accommodation near Cheshire attractions

Cheshire Travel Info

Number of hotels
872
Highest price
£222
Lowest price
£61
Known attractions
Jiminy Peak Mountain Resort, Berkshire Museum and Colonial Theatre
Hotels with family-friendly amenities
5
Hotels with skiing
12

Frequently asked questions

What's the best place to stay in Cheshire?

Located 12.2 mi (19.6 km) from the heart of Cheshire, The Yankee, Trademark Collection by Wyndham is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Life House Berkshires and Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel. See all available top hotels, or vacation rentals in Cheshire.

What are some of the best holiday rentals that Cheshire has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Cheshire is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. See all vacation rentals in Cheshire.

If I need to cancel my hotel reservation in Cheshire, will I receive a refund?

Yes! Most room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.

What are some hotels with pools in Cheshire?

Modern Berkshires home + private pool: Provides TVs, an outdoor pool and air conditioning. Vacation Village in the Berkshires and Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel are two additional hotels that feature an on-site pool.

What is staying in Cheshire like?

Visitors can enjoy all that Cheshire has to offer, including the ski areas, restaurants and lake views. Tourists can also enjoy so much more including its shopping. In Cheshire, there are 3 hotels and other accommodation options to choose from. Find out more about Cheshire.

What is there to see in Cheshire?

A couple of favourite places to visit are Mount Greylock State Reservation and St Mary's of the Assumption Church. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Take a look at what more there is to see and do in Expedia's Cheshire guide.

What's the seasonal weather in Cheshire?

The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 23 cm of snowfall.

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