Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 590,000 properties worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Check prices on hotels in The Berkshires

Tonight Tonight Jun 20 - Jun 21
This weekend This weekend Jun 22 - Jun 24
Next weekend Next weekend Jun 29 - Jul 1

Featured The Berkshires Shopping Hotels

See all 144 Properties in The Berkshires
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
    3.5 out of 5.0
     
     
    3.6 out of 5 (501 reviews)
    Great location, great indoor poolThis hotel is in a great location in the heart of Pittsfield with views of the Berkshires. It is currently being refurbished and we stayed in a basic room that was a little dated but clean and comfortable. The staff was friendly and the indoor pool area is really nice and connected to the restaurant. ...
    Apr 25, 2018

    Crowne Plaza Pittsfield-Berkshires$91

    Crowne Plaza Pittsfield-Berkshires$91
    Travelodge by Wyndham Great Barrington Berkshires

    Travelodge by Wyndham Great Barrington Berkshires

    400 Stockbridge Rd, Great Barrington
    • Free Cancellation
    • Reserve now, pay when you stay
    2.0 out of 5.0
     
     
    3.2 out of 5 (308 reviews)
    Wonderful place! Excellent bargain, clean rooms, free continental breakfast, and an exceptionally warm, gracious and accommodating extended family running the place. Originally planned to stay for just one night but extended for three additional days.
    Mar 13, 2018

    Travelodge by Wyndham Great Barrington Berkshires$75

    Travelodge by Wyndham Great Barrington Berkshires$75
    Chambery Inn

    Chambery Inn

    199 Main St, Lee
      3.0 out of 5.0
       
       
      4.7 out of 5 (152 reviews)
      Lovely but ....We have stayed at the Chamberay Inn many times and enjoy our stay very much. We have stayed in many of their various rooms. This stay, however, the room was an awkward design. You couldn’t really watch the TV for the bed and he two chairs were too far away from the TV to watch comfortably. The set ...
      Feb 17, 2018

      Chambery Inn$150

      Chambery Inn$150
      Jiminy Peak Mountain Resort

      Jiminy Peak Mountain Resort

      37 Corey Rd, Hancock
        3.0 out of 5.0
         
         
        4.0 out of 5 (516 reviews)
        Ski resortShoppes and most restaurants on resort are only open seasonally, facilities are a little dated, but seems like it would be great to stay at when everything else is open. But there were awesome things to do in towns nearby.
        Apr 17, 2018

        Jiminy Peak Mountain Resort$129

        Jiminy Peak Mountain Resort$129
        Topia Inn - An Organic Oasis

        Topia Inn - An Organic Oasis

        10 Pleasant Street, Adams
          2.5 out of 5.0
           
           
          4.5 out of 5 (18 reviews)
          Cozy bed and breakfast in the Berkshires.Check in was arranged via email prior to our arrival. We were greeted at the door and given a brief tour of the hotel. The vegan breakfast each morning was delicious and unique, if a little small. They served very high quality coffee, as well. We stayed in the Zen room the first night, and the Aloha ...
          Sep 25, 2017

          Topia Inn - An Organic Oasis$266

          Topia Inn - An Organic Oasis$266
          Yankee Inn

          Yankee Inn

          461 Pittsfield Rd, Lenox
          • Free Cancellation
          • Reserve now, pay when you stay
          2.5 out of 5.0
           
           
          3.9 out of 5 (526 reviews)
          Nice place. Convenient location.Very nice staff. Clean room with good beds and nicely upgraded bathroom. Good breakfast with made to order omelets. Only drawback to my 1st floor room was very loud upstairs guests. Floor/ceiling does not insulate sound well.
          Jun 4, 2018

          Yankee Inn$92

          Yankee Inn$92
          Days Inn by Wyndham Great Barrington

          Days Inn by Wyndham Great Barrington

          372 Main Street, Great Barrington
            2.0 out of 5.0
             
             
            3.8 out of 5 (412 reviews)
            Great staffHotel is good and the staff there are excellant and go far and beyond for the guests
            Jun 2, 2018

            Days Inn by Wyndham Great Barrington$101

            Days Inn by Wyndham Great Barrington$101
            Heart of Lenox!! - Renovated Downtown Apartment

            Heart of Lenox!! - Renovated Downtown Apartment

            , Lenox
               
               
              4.9 out of 5 (15 reviews)
              A peaceful stayThis was our second time here. Attentive owner/manager, clean place, great for relaxing with family, cooking, sauntering around town.
              Mar 27, 2018
              Black Swan Inn, an Ascend Collection Hotel

              Black Swan Inn, an Ascend Collection Hotel

              435 Laurel St, Lee
                3.0 out of 5.0
                 
                 
                4.1 out of 5 (407 reviews)
                Nice, cozy hotel on the waterfront Nice cozy hotel on with option to select rooms with spacious patios overlooking the lake. Unfortunately despite hotel stating that it includes breakfast, breakfast selection is lacking is next to nothing. It consists of some bagels, bread, and yogurt, maybe some cereal but that is all. A nice breakfast ...
                Jun 2, 2018

                Black Swan Inn, an Ascend Collection Hotel$103

                Black Swan Inn, an Ascend Collection Hotel$103
                Holiday Inn Berkshires

                Holiday Inn Berkshires

                40 Main St, North Adams
                • Free Cancellation
                • Reserve now, pay when you stay
                3.0 out of 5.0
                 
                 
                4.1 out of 5 (473 reviews)
                Needs updatesStaff was extremely friendly! Room was clean and bedding clean. Bathroom was very dark. Lighting poor and bathroom needed updates. Walls are SO thin! I could hear people above me and beside me having conversations.
                May 20, 2018

                Holiday Inn Berkshires$117

                Holiday Inn Berkshires$117
                Super 8 by Wyndham Lee/Berkshires/Outlet Area

                Super 8 by Wyndham Lee/Berkshires/Outlet Area

                170 Housatonic Street, Lee
                • Free Cancellation
                • Reserve now, pay when you stay
                2.0 out of 5.0
                 
                 
                3.6 out of 5 (292 reviews)
                Great location, perfect for our tripNice clean room, friendly check in staff. Walking distance to shops and restaurants in Lee.
                Jun 19, 2018

                Super 8 by Wyndham Lee/Berkshires/Outlet Area$76

                Super 8 by Wyndham Lee/Berkshires/Outlet Area$76
                Interior Designers Botanical Garden Hideaway

                Interior Designers Botanical Garden Hideaway

                , PITTSFIELD
                   
                   
                  4.7 out of 5 (21 reviews)
                  Beautiful propertyWe enjoyed our stay here very much. Gorgeous garden and beautifully decorated interior. It was a pleasure whenever we had a chance to interact with the owner, Sandra. A larger fridge and a sink in the kitchen area would be a big plus. We have a few photos to share. Let us know how best to send them. ...
                  Sep 29, 2017
                  Wagon Wheel Inn

                  Wagon Wheel Inn

                  484 Pittsfield Rd, Lenox
                    2.0 out of 5.0
                     
                     
                    3.6 out of 5 (222 reviews)
                    A quiet, little bargain gemWhile there's nothing in particular about the exterior that would suggest that it's anything more than just another older, low-budget motor hotel, my room, though small, was very comfortable, well-maintained, clean, nicely furnished and quiet. And the staff was very friendly and helpful. I found ...
                    May 17, 2018

                    Wagon Wheel Inn$53

                    Wagon Wheel Inn$53
                    Beautiful, Cozy Log Home On The Hill Overlooking The Town

                    Beautiful, Cozy Log Home On The Hill Overlooking The Town

                    , Great Barrington
                       
                       
                      4.9 out of 5 (20 reviews)
                      Beautiful cabin. Good amenitiesWe were there for a four day family weekend and really enjoyed our stay. Lots of light, comfortable beds and couches, good appliances and clean. Trish was very prompt in responding to any questions we had and was just a phone call away Thanks
                      Apr 22, 2018
                      Lantern House Motel

                      Lantern House Motel

                      256 Stockbridge Road, Great Barrington
                        2.5 out of 5.0
                         
                         
                        4.1 out of 5 (170 reviews)
                        Happy with my stay Clean basic low cost good location I would stay there again
                        Jun 8, 2018

                        Lantern House Motel$65

                        Lantern House Motel$65
                        House On Main Street

                        House On Main Street

                        1120 Main St, Williamstown
                          3.0 out of 5.0
                           
                           
                          4.4 out of 5 (125 reviews)
                          Nice B&B right on the Williams campus.The room was clean, the beds comfortable, the breakfast tasty. The place is extremely convenient to campus. We used a shared bathroom, and it was totally fine. Never had any issues. It was like staying in the guest room of a family friend.
                          Feb 20, 2018

                          House On Main Street$111

                          House On Main Street$111
                          Eastgate Inn B&B

                          Eastgate Inn B&B

                          207 West Street, Lenox
                            2.5 out of 5.0
                             
                             
                            4.6 out of 5 (17 reviews)
                            Great place to stay!Great location and the innkeeper was very friendly. Very quiet and quaint.
                            Jun 10, 2018

                            Eastgate Inn B&B$130

                            Eastgate Inn B&B$130
                            Hotel On North

                            Hotel On North

                            297 North Street, Pittsfield
                              3.5 out of 5.0
                               
                               
                              4.8 out of 5 (153 reviews)
                              boutique hotel, wonderful personal touches.This is a special hotel clearly designed with love of hospitality and environment. Gorgeous hardwood floors throughout, large game room for kids of all ages, spacious clean guest room with coffee, robes, water ... Design matches Berkshire / hipster vibe - a lot of fun for this mother daughter get ...
                              Mar 31, 2018

                              Hotel On North$149

                              Hotel On North$149
                              Williamstown Motel

                              Williamstown Motel

                              295 Main Street, Williamstown
                              • Free Cancellation
                              • Reserve now, pay when you stay
                              2.0 out of 5.0
                               
                               
                              3.8 out of 5 (211 reviews)
                              Economical, clean and updated rooms,Close to everything in Williamstown and nearby outdoors activities. The price is right and staff is helpful.
                              May 18, 2018

                              Williamstown Motel$84

                              Williamstown Motel$84
                              Map

                              Recently booked Shopping Hotels in The Berkshires

                              Super 8 by Wyndham Lee/Berkshires/Outlet Area
                              2.0 out of 5.0
                              Last booking: 4 hours ago
                              Cozy Corner Motel
                              2.0 out of 5.0
                              Last booking: 5 hours ago
                              Wyndham Bentley Brook
                              3.0 out of 5.0
                              Last booking: 5 hours ago
                              Cranwell Spa and Golf Resort
                              3.5 out of 5.0
                              Last booking: 5 hours ago
                              Shaker Mill Inn
                              2.5 out of 5.0
                              Last booking: 6 hours ago
                              Travelodge by Wyndham Great Barrington Berkshires
                              2.0 out of 5.0
                              Last booking: 6 hours ago
                              Jiminy Peak Mountain Resort
                              3.0 out of 5.0
                              Last booking: 6 hours ago
                              Green Valley Motel
                              2.0 out of 5.0
                              Last booking: 6 hours ago
                              Pleasant Valley Motel West Stockbridge
                              2.0 out of 5.0
                              Last booking: 7 hours ago

                              Pocket Guide: Shopping Hotels in The Berkshires

                              Search for hotels in The Berkshires on Expedia. You can easily find your hotels in The Berkshires using one of the methods below:

                              • View our selection of featured hotels in The Berkshires
                              • Use the map to find hotels in the The Berkshires neighborhood you prefer
                              • Use the filters to see hotels in a specific area of The Berkshires, select a specific theme, brand, or hotel class from basic (1 Star) to luxury hotels (5 Stars) in The Berkshires
                              • Enter your travel dates to view the best deals on hotels in The Berkshires - while they last