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Cheshire

Welcome to Cheshire, a great destination to add to your next The Berkshires vacation.

Packages in Cheshire

Booking both your flights and a place to stay is really simple with Expedia. Booking your desired flights and accommodations are the ingredients for a good vacation. Combining them together with us into a single package deal is a recipe for success that takes out the stress and saves you money. That means added cash for your Cheshire trip!

Receive savings of up to 17% by securing a package deal.

We enjoy making going on a vacation easy and simple if you select from our global range of about 400 airline partners and 321,000 worldwide hotels.

Check out some of the best prices ever at Expedia and book the trip you've been pondering. Your family will thank you for it.

You can delay your travel itineraries with us because we don't charge cancellation fees for almost all of our bookings.

Cheshire Vacation Packages

From Cheshire, Albany is 30 miles west, and Hartford is 60 miles southeast.

When the ocean breeze starts calling you, pack a bag and travel to Crystal Lake Sandy Beach, 60 miles away.

Nature lovers come to this part of the country to admire its marvelous natural landscapes. Experience the magic for yourself at Great Falls Discovery Center and Molly Stark State Park, 30 miles and 25 miles away from Cheshire, respectively.

Joseph L Bruno Stadium is 30 miles to the west of Cheshire. It's here you can watch the Tri-City ValleyCats play a home game. Notice the home team's colors of red, grey and white.

From hitting the slopes to building snowmen, ski resorts have something for the whole family. Cheshire is close to two, Mount Snow and Ski Sundown, merely 30 miles and 50 miles from the city.

Many vacationers recommend visiting St Mary's of the Assumption Church.

Albany International Airport is your closest airport at about 35 miles to the west, so make sure you give yourself plenty of time.

Accommodation in Cheshire

Cheshire lodging options could be limited. Be sure to book ahead with Expedia to find the right room for you.

The Spring's Inn and Topia Inn - An Organic Oasis are the main accommodation options in and around Cheshire.


Top Hotel Deals

See all 129 Hotels in Cheshire
Harbour House Inn £103
Harbour House Inn

Harbour House Inn

725 North State Road, Cheshire
     
    4.9
    of 5, from 8 reviews
    3.5 out of 5.0

    Situated in the mountains, this bed & breakfast is within 6 miles (10 km) of Topia Arts Center, East Hoosac Quaker Meetinghouse and Susan B. Anthony Birthplace Museum. Mount Greylock and Western Gateway Heritage State Park are also within 9 miles (15 km).

    Vacation Village in the Berkshires £76
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Hancock
       
      4.2
      of 5, from 807 reviews
      3.0 out of 5.0

      Situated in Hancock, this condo is 5.8 mi (9.3 km) from Mount Greylock State Reservation Visitor Center and within 12 miles (20 km) of Waubeeka Golf Links and New Lebanon Library. Mount Lebanon Shaker Village and Berkshire Athenaeum are also within 12 miles (20 km).

      Jiminy Peak Mountain Resort £97
      Jiminy Peak Mountain Resort

      Jiminy Peak Mountain Resort

      37 Corey Rd, Hancock
         
        4.0
        of 5, from 513 reviews
        3.0 out of 5.0

        Located in the mountains, this Hancock condominium resort offering ski-in/ski-out access is 6.1 mi (9.8 km) from Mount Greylock State Reservation Visitor Center and within 16 mi (25 km) of Waubeeka Golf Links and Canoe Meadows Wildlife Sanctuary. New Lebanon Library and Mount Lebanon Shaker Village are also within 12 miles (20 km).

        Yankee Inn £56
        Yankee Inn

        Yankee Inn

        461 Pittsfield Rd, Lenox
           
          3.9
          of 5, from 509 reviews
          2.5 out of 5.0

          Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 miles (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. Lenox Library and Bousquet Ski Area are also within 3 miles (5 km).

          Courtyard by Marriott Lenox Berkshires £81
          Courtyard by Marriott Lenox Berkshires

          Courtyard by Marriott Lenox Berkshires

          70 Pittsfield Rd, Lenox
             
            4.5
            of 5, from 57 reviews
            3.0 out of 5.0

            Situated in Lenox, this hotel is within 2 miles (3 km) of Kennedy Park, Lenox Library and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 3 miles (5 km).

            Hampton Inn & Suites Berkshires Lenox £145
            Hampton Inn & Suites Berkshires Lenox

            Hampton Inn & Suites Berkshires Lenox

            445 Pittsfield Rd, Lenox
               
              4.6
              of 5, from 360 reviews
              2.5 out of 5.0

              Situated in a rural location, this hotel is within 2 miles (3 km) of Arrowhead Museum, Kennedy Park and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary and Canoe Meadows Wildlife Sanctuary are also within 3 miles (5 km).

              Best Western Plus Berkshire Hills Inn & Suites £64
              Best Western Plus Berkshire Hills Inn & Suites

              Best Western Plus Berkshire Hills Inn & Suites

              1350 W Housatonic St, Pittsfield
                 
                4.1
                of 5, from 445 reviews
                2.5 out of 5.0

                Located in the heart of Pittsfield, this hotel is 1.7 mi (2.8 km) from Hancock Shaker Village and 2.9 mi (4.7 km) from Bousquet Ski Area. Colonial Theater and Berkshire Museum are also within 6 miles (10 km).

                The Red Lion Inn £104
                The Red Lion Inn

                The Red Lion Inn

                30 Main Street, Stockbridge
                   
                  4.4
                  of 5, from 174 reviews
                  3.5 out of 5.0

                  This family-friendly Stockbridge hotel is located in the historical district, within a 15-minute walk of Mission House, Berkshire Theatre Festival and Naumkeag. Berkshire Botanical Garden and National Shrine of the Divine Mercy are also within 3 miles (5 km).

                  Top Deals on Flights

                  These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.