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Cheshire Vacation Packages

In order to see all that there is to see in Cheshire, it's worth doing a bit of research before you visit.

Save Time and Money with a Cheshire Package Deal

Save money with Expedia by pairing your lodging and flight bookings. We love to ease your stresses by pairing up your accommodation and flight bookings for even more great savings. Think of everything you can do in Cheshire with the extra cash.

Approximately 15% can be saved when you book your package deal with us.

With us, you will have up to 400 partner airlines and 321,000 hotels worldwide from all over the world to make your choice from.

Your Cheshire trip will be that much nicer with Expedia's prices.

Don't worry about altering your vacation plans, as we do not charge additional cancellation fees for almost all of our bookings.

Cheshire Vacation Packages

The notable city of Montpelier sits 120 miles to the north of Cheshire.

If you enjoy the great outdoors, check out one of the Cheshire region's natural areas. Mount Greylock is 5 miles away from Cheshire, while Albany Visitors Centre lies 30 miles away.

If you have an interest in religion, be sure to see St Mary's of the Assumption Church.

Sports lovers should make the trip to see the Tri-City ValleyCats play a home game at Joseph L Bruno Stadium. It's in Albany, 30 miles west of Cheshire. If you want to support the hometown heroes, wear some red, grey and white.

Get your blood pumping on some fresh snow! Cheshire is in the vicinity of two main ski runs, Okemo Mountain Resort and Mount Snow.

The Mass MoCA and the Topia Arts Centre are just a handful of the interesting attractions in Adams, a destination 5 miles away from Cheshire. Another possibility is New Ashford. It's about 5 miles from Cheshire, and is the home of Mount Greylock State Reservation Visitor Centre and Jiminy Peak Mountain Resort.

Pittsfield is 9 miles to the southwest of Cheshire. This regional hub is known for the Arrowhead Museum, Bousquet Ski Area and Canoe Meadows Wildlife Sanctuary. Don't rush back until you've also explored the Berkshire Athenaeum and the Berkshire Museum.

Enjoy the cuisine of The Berkshires by taking your taste buds on a tour of its enticing cafés and restaurants.

Make sure you look out for the more popular regional ingredients, like cod and clams.

No culinary experience can be complete until you've had something sweet. Frappe will surely fit the bill.

The 4th of July is the day when the whole country will celebrate Independence Day. You're sure to find plenty of festivities to enjoy if you're visiting at that time.

The most convenient airport, Bradley International Airport (BDL), is about 50 miles to the southeast.

Accommodation in Cheshire

We suggest you book a room in advance, as presently there is only a small selection of Cheshire lodgings to choose from.

The Spring's Inn and The Weathervane Motel are among the best options in and around Cheshire.


Top Hotel Deals

See all 129 properties in Cheshire
Harbour House Inn £139
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. Savoy Mountain State Forest and Western Gateway Heritage State Park are also within 9 miles (15 km).

    Hilton Garden Inn Lenox Pittsfield
    Hilton Garden Inn Lenox Pittsfield

    Hilton Garden Inn Lenox Pittsfield

    1032 South Street, Pittsfield
       
      4.7
      of 5, from 123 reviews
      3.0 out of 5.0

      Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 miles (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and Berkshire Museum are also within 3 miles (5 km).

      Yankee Inn £72
      Yankee Inn

      Yankee Inn

      461 Pittsfield Rd, Lenox
         
        3.9
        of 5, from 528 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).

        The Orchards Hotel £167
        The Orchards Hotel

        The Orchards Hotel

        222 Adams Rd, Williamstown
           
          4.4
          of 5, from 303 reviews
          3.5 out of 5.0

          Situated in a rural location, this hotel is within 1 mile (2 km) of Hopkins Observatory, Williams College Museum of Art and Chapin Library of Rare Books and Manuscripts. Williams College and 62 Center for Theater and Dance are also within 1 mile (2 km).

          Berkshire Hills Country Inn
          Berkshire Hills Country Inn

          Berkshire Hills Country Inn

          1146 Cold Spring Road, Williamstown
             
            4.2
            of 5, from 99 reviews
            2.5 out of 5.0

            Situated in Williamstown, this hotel is within 3 miles (5 km) of Williamstown Historical Museum, Waubeeka Golf Links and 62 Center for Theater and Dance. Chapin Library of Rare Books and Manuscripts and Williams College Museum of Art are also within 3 miles (5 km).

            Hampton Inn & Suites Berkshires Lenox
            Hampton Inn & Suites Berkshires Lenox

            Hampton Inn & Suites Berkshires Lenox

            445 Pittsfield Rd, Lenox
               
              4.6
              of 5, from 368 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).

              Vacation Village in the Berkshires £96
              Vacation Village in the Berkshires

              Vacation Village in the Berkshires

              276 Brodie Mountain Rd, Hancock
                 
                4.2
                of 5, from 819 reviews
                3.0 out of 5.0

                Situated in Hancock, this condo is within 9 miles (15 km) of Mount Greylock State Reservation Visitor Center, Pittsfield State Forest and Waubeeka Golf Links. New Lebanon Library and Berkshire Athenaeum are also within 12 miles (20 km).

                Super 8 by Wyndham Lee/Berkshires/Outlet Area £57
                Super 8 by Wyndham Lee/Berkshires/Outlet Area

                Super 8 by Wyndham Lee/Berkshires/Outlet Area

                170 Housatonic Street, Lee
                   
                  3.6
                  of 5, from 293 reviews
                  2.0 out of 5.0

                  Situated in Lee, this motel is within a 15-minute walk of Lee Prime Outlets, Lee Library and Animagic Museum of Animation. Greenock Country Club and Beartown State Forest are also within 3 miles (5 km).

                  Top Deals on Flights

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