Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Start by selecting your hotel
Start by selecting your hotel

Save up to $603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

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


Pittsfield Vacation Travel Guide

Accommodation in Pittsfield

Pre-booking the perfect place to stay often equates to vacation bliss. You can check out a selection of the best accommodation in Pittsfield through Expedia's easy-to-use Pittsfield hotels guide.

If you feel like splashing out for a special occasion, be sure to check out the rates and amenities at the Crowne Plaza Pittsfield-Berkshires, at 1 West St, and the White Horse Inn, at 378 South St. If you discover that those don't quite match your budget and style, the Best Western Plus Berkshire Hills Inn & Suites and the Econo Lodge are two more economical hotels that may offer all the services and features you need.

It’s easy to book the getaway of your dreams when you search through our selection of Pittsfield vacations. Our goal? To create the perfect trip for you by providing the largest selection of vacation packages. Confidently book your getaway thanks to our trustworthy recommendations and verified consumer reviews from travelers just like you. Personalize your Pittsfield package with our myriad of hotel rooms and flight tickets, which help to create a vacation specifically for you. Simply sort through our selection and pick and choose the elements that best suit your preferences and price range.

Because we offer the best rates, you can book your travel reservations knowing you won’t find lower prices elsewhere. These discounts are so great, you’ll feel like you gained the title of the ultimate bargain hunter with our Pittsfield vacation package deals. Whether you’re looking to book multiple flights, stay at the fanciest hotel, or explore the hottest local attractions, you’ll find discounted travel arrangements within your budget right here. You shouldn’t have a care in the world when you go on vacation, so our discounts allow you to rest easy without giving your bank account a second thought. Save money on your vacation today and revel in your much-deserved getaway tomorrow.


Top Hotel Deals

See all 163 Hotels in Pittsfield
Best Western Plus Berkshire Hills Inn & Suites $86
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 mi (10 km).

    Crowne Plaza Pittsfield-Berkshires $89
    Crowne Plaza Pittsfield-Berkshires

    Crowne Plaza Pittsfield-Berkshires

    1 West St, Pittsfield
       
      3.6
      of 5, from 473 reviews
      3.5 out of 5.0

      Located in the heart of Pittsfield, this hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife Sanctuary and Arrowhead Museum are also within 3 mi (5 km).

      Hotel On North $135
      Hotel On North

      Hotel On North

      297 North Street, Pittsfield
         
        4.8
        of 5, from 144 reviews
        3.5 out of 5.0

        Situated in Pittsfield, this hotel is within a 10-minute walk of Berkshire Museum, Berkshire Athenaeum, and Colonial Theater. Canoe Meadows Wildlife Sanctuary is 2.1 mi (3.3 km) away.

        Hilton Garden Inn Lenox/Pittsfield $110
        Hilton Garden Inn Lenox/Pittsfield

        Hilton Garden Inn Lenox/Pittsfield

        1032 South Street, Pittsfield
           
          4.7
          of 5, from 110 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 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and Berkshire Museum are also within 3 mi (5 km).

          Berkshire Mountain Lodge $150
          Berkshire Mountain Lodge

          Berkshire Mountain Lodge

          8 Dan Fox Dr, Pittsfield
             
            3.0 out of 5.0

            Situated in Pittsfield, this lodge is close to Arrowhead Museum, Bousquet Ski Area, and Canoe Meadows Wildlife Sanctuary. Local attractions also include Kennedy Park and Colonial Theater.

            Berkshire Inn $60
            Berkshire Inn

            Berkshire Inn

            150 W Housatonic St, Pittsfield
               
              3.5
              of 5, from 152 reviews
              2.0 out of 5.0

              Located in the heart of Pittsfield, this motel is within a 15-minute walk of Colonial Theater and Berkshire Museum. Berkshire Athenaeum and Canoe Meadows Wildlife Sanctuary are also within 2 mi (3 km).

              Yankee Suites Extended Stay $85
              Yankee Suites Extended Stay

              Yankee Suites Extended Stay

              20 W Housatonic St., Pittsfield
                 
                4.4
                of 5, from 81 reviews
                4.0 out of 5.0

                Situated in Pittsfield, this guesthouse is within a 5-minute walk of Colonial Theater and Berkshire Museum. Berkshire Athenaeum and Canoe Meadows Wildlife Sanctuary are also within 2 mi (3 km).

                Econo Lodge $69
                Econo Lodge

                Econo Lodge

                16 Cheshire Road, Pittsfield
                   
                  2.7
                  of 5, from 236 reviews
                  1.5 out of 5.0

                  Situated in the suburbs, this motel is 1.6 mi (2.6 km) from Crane Museum of Papermaking and within 6 mi (10 km) of Berkshire Athenaeum and Colonial Theater. Berkshire Museum and Canoe Meadows Wildlife Sanctuary are also within 6 mi (10 km).