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Compare Cheap Hotels in Cheshire

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Jan 24 - Jan 26
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Jan 31 - Feb 2

Cheap Cheshire Hotels

Price for 1 night 2 adults*

Seven Hills Inn

Seven Hills Inn

40 Plunkett Street, Lenox, MA
    4.0 out of 5.0
     
     

    Located in Lenox, Seven Hills Inn is within a 10-minute drive of Tanglewood Music Center and Lee Prime Outlets.

    $109

    Per night/room

    Jan 20 - Jan 21

    The Williams Inn

    The Williams Inn

    101 Spring Street, Williamstown, MA
      4.0 out of 5.0
       
       

      Located in Williamstown, The Williams Inn is within a 15-minute drive of Williams College and Mass MoCA.

      $169

      Per night/room

      Jan 20 - Jan 21

      Yankee Suites Extended Stay

      Yankee Suites Extended Stay

      20 W Housatonic St., Pittsfield, MA
        4.0 out of 5.0
         
         

        With a stay at Yankee Suites Extended Stay in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Berkshire Museum.

        $80

        Per night/room

        Jan 20 - Jan 21

        33 Main

        33 Main

        33 Main Street, Lenox, MA
          4.0 out of 5.0
           
           

          With a stay at 33 Main, you'll be centrally located in Lenox, within a 5-minute drive of Tanglewood Music Center and Lenox Library.

          $250

          Per night/room

          Jan 22 - Jan 23

          The Inn at Stockbridge

          The Inn at Stockbridge

          30 East Street, Stockbridge, MA
            4.0 out of 5.0
             
             

            With a stay at The Inn at Stockbridge in Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Berkshire Theatre Festival.

            $179

            Per night/room

            Jan 20 - Jan 21

            Stockbridge Country Inn

            Stockbridge Country Inn

            26 Glendale Road, RR 183, Stockbridge, MA
              4.5 out of 5.0
               
               

              With a stay at Stockbridge Country Inn in Stockbridge, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Chesterwood.

              Stockbridge Country InnGet Rates

              Garden Gables Inn

              Garden Gables Inn

              135 Main St, Lenox, MA
                4.0 out of 5.0
                 
                 

                With a stay at Garden Gables Inn in Lenox, you'll be in the historical district, within a 5-minute drive of Tanglewood Music Center and Lenox Library.

                $199

                Per night/room

                Jan 20 - Jan 21

                Devonfield Inn B&B

                Devonfield Inn B&B

                85 Stockbridge Rd., Lee, MA
                  4.0 out of 5.0
                   
                   

                  With a stay at Devonfield Inn B&B in Lee, you'll be next to a golf course, within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

                  $179

                  Per night/room

                  Jan 19 - Jan 20

                  Lakehouse Inn

                  Lakehouse Inn

                  615 Laurel St., Lee, MA
                    4.0 out of 5.0
                     
                     

                    With a stay at Lakehouse Inn in Lee, you'll be on the beach, within a 10-minute drive of Tanglewood Music Center and Animagic Museum of Animation.

                    $150

                    Per night/room

                    Jan 23 - Jan 24

                    Hampton Terrace Inn

                    Hampton Terrace Inn

                    91 Walker Street, Lenox, MA
                      4.0 out of 5.0
                       
                       

                      With a stay at Hampton Terrace Inn in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and Ventfort Hall Mansion and Gilded Age Museum.

                      $199

                      Per night/room

                      Jan 24 - Jan 25

                      Rose and Goat Retreat

                      Rose and Goat Retreat

                      9 Moores Rd, North Adams, MA
                        4.0 out of 5.0
                         
                         

                        With a stay at Rose and Goat Retreat in North Adams, you'll be near ski lifts, within a 15-minute drive of Mass MoCA and Savoy Mountain State Forest.

                        Rose and Goat RetreatGet Rates

                        1862 Seasons on Main Bed and Breakfast

                        1862 Seasons on Main Bed and Breakfast

                        47 Main Street, Stockbridge, MA
                          4.5 out of 5.0
                           
                           

                          With a stay at 1862 Seasons on Main Bed and Breakfast in Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Ski Butternut.

                          1862 Seasons on Main Bed and BreakfastGet Rates

                          Map

                          Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.

                          Most Recent Cheshire Hotel Reviews

                          CheapTickets Verified Review
                          5 out of 5
                          My husband and I stopped here from our long road trip and we were glad we found this hotel. It is located in a safe area especially being right across the police station. I can’t imagine anything shady happens there. Our hotel room was clean, warm, and comfortable with really nice toiletries provided. Sonal checked us in and out of the hotel, and was such a sweet and kind person. We enjoyed getting to know her and a little more about that college town. I would definitely recommend this stay for other couples and families.

                          A verified traveler stayed at Cozy Corner Motel

                          Posted 2 months ago
                          Open Cozy Corner Motel hotel guest reviews
                          CheapTickets Verified Review
                          4 out of 5
                          The folks at the front desk are exceptional Very friendly and helpful

                          A verified traveler stayed at Yankee Inn

                          Posted 4 months ago
                          Open Yankee Inn hotel guest reviews
                          CheapTickets Verified Review
                          3 out of 5
                          Ok. It was clean but the staff/ manager called the day before asked if we needed all 3 rooms. I told him NO. We only needed 2 of the 3. This was in time for the cancellation clause. When i checked in he gave me 3 keys. I told him NO, we had talked and cancelled. He said i would need to have called expedia to do that. I didn't book with them. He would not cancel it and was very gruff and rude.

                          A verified traveler stayed at Pleasant Valley Motel West Stockbridge

                          Posted 6 months ago
                          Open Pleasant Valley Motel West Stockbridge hotel guest reviews
                          CheapTickets Verified Review
                          4 out of 5
                          Need a coffee maker in the room. Nice location all needs are close by.

                          A verified traveler from Hopkinton, us stayed at Berkshire Inn

                          Posted 10 months ago
                          Open Berkshire Inn hotel guest reviews
                          CheapTickets Verified Review
                          4 out of 5
                          very nice ad immaculately Clean looks like and old time motel but the room was exceptionally clean and the staff was really friendly

                          A verified traveler from watertown stayed at Wagon Wheel Inn

                          Posted 1 year ago
                          Open Wagon Wheel Inn hotel guest reviews
                          CheapTickets Verified Review
                          5 out of 5
                          Was in town on business and was the only hotel left for the night. Was very clean and staff was very professional

                          A verified traveler stayed at Best Western Plus Berkshire Hills Inn & Suites

                          Posted 1 year ago
                          Open Best Western Plus Berkshire Hills Inn & Suites hotel guest reviews
                          See a list of all hotels in Cheshire

                          An Airport

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                          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.