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The Berkshires Vacations

Pack those stellar shades. We have The Berkshires vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to The Berkshires – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with The Berkshires vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to The Berkshires

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great The Berkshires vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows The Berkshires well.

Top Hotel Deals

See all 148 Hotels in The Berkshires
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

1032 South Street, Pittsfield
    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 ...

    Hilton Garden Inn Lenox Pittsfield$110

    Hilton Garden Inn Lenox Pittsfield$110
    Crowne Plaza Pittsfield-Berkshires

    Crowne Plaza Pittsfield-Berkshires

    1 West St, Pittsfield
      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 ...

      Crowne Plaza Pittsfield-Berkshires$96

      Crowne Plaza Pittsfield-Berkshires$96
      The Red Lion Inn

      The Red Lion Inn

      30 Main Street, Stockbridge
        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. ...

        The Red Lion Inn$139

        The Red Lion Inn$139
        The Orchards Hotel

        The Orchards Hotel

        222 Adams Rd, Williamstown
          3.5 out of 5.0
           
           

          Situated in a rural location, this hotel is within 1 mi (2 km) of Hopkins Observatory, Williams College Museum of Art, and Chapin Library of Rare Books and Manuscripts. ...

          The Orchards Hotel$159

          The Orchards Hotel$159
          Yankee Inn

          Yankee Inn

          461 Pittsfield Rd, Lenox
            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 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. ...

            Yankee Inn$92

            Yankee Inn$92
            Berkshire Hills Country Inn

            Berkshire Hills Country Inn

            1146 Cold Spring Road, Williamstown
              2.5 out of 5.0
               
               

              Situated in Williamstown, this hotel is within 3 mi (5 km) of Williamstown Historical Museum, Waubeeka Golf Links, and 62 Center for Theater and Dance. Chapin ...

              Holiday Inn Berkshires

              Holiday Inn Berkshires

              40 Main St, North Adams
                3.0 out of 5.0
                 
                 

                Located in the heart of North Adams, this hotel is within a 10-minute walk of Mass MoCA, North Adams Public Library, and Western Gateway Heritage State Park. ...

                Holiday Inn Berkshires$111

                Holiday Inn Berkshires$111
                Vacation Village in the Berkshires

                Vacation Village in the Berkshires

                276 Brodie Mountain Rd, Hancock
                  3.0 out of 5.0
                   
                   

                  Situated in Hancock, this condo building is 5.8 mi (9.3 km) from Mount Greylock State Reservation Visitor Center and within 12 mi (20 km) of Waubeeka Golf Links ...

                  Vacation Village in the Berkshires$135

                  Vacation Village in the Berkshires$135
                  Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

                  Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

                  249 Stockbridge Rd, Great Barrington
                    2.5 out of 5.0
                     
                     

                    This family-friendly Great Barrington hotel is located in the mountains, within 2 mi (3 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. Ski Butternut ...

                    Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires$135

                    Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires$135
                    Courtyard by Marriott Lenox Berkshires

                    Courtyard by Marriott Lenox Berkshires

                    70 Pittsfield Rd, Lenox
                      3.0 out of 5.0
                       
                       

                      Situated in Lenox, this hotel is within 2 mi (3 km) of Kennedy Park, Lenox Library, and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded ...

                      Courtyard by Marriott Lenox Berkshires$134

                      Courtyard by Marriott Lenox Berkshires$134

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.