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Great Barrington Vacations

Pack those stellar shades. We have Great Barrington 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 Great Barrington – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Great Barrington 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 Great Barrington

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 Great Barrington 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 Great Barrington well.

Top Hotel Deals

See all 171 Hotels in Great Barrington
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
    Days Inn by Wyndham Great Barrington

    Days Inn by Wyndham Great Barrington

    372 Main Street, Great Barrington
      2.0 out of 5.0
       
       

      Situated in Great Barrington, this motel is within 1 mi (2 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. W.E.B. Du Bois Boyhood Homesite is ...

      Days Inn by Wyndham Great Barrington$81

      Days Inn by Wyndham Great Barrington$81
      The Briarcliff Motel

      The Briarcliff Motel

      506 Stockbridge Road, Great Barrington
        2.0 out of 5.0
         
         

        Situated in Great Barrington, this motel is within 6 mi (10 km) of Mission House, Berkshire Theatre Festival, and Naumkeag. National Shrine of the Divine Mercy ...

        The Briarcliff Motel$90

        The Briarcliff Motel$90
        Lantern House Motel

        Lantern House Motel

        256 Stockbridge Road, Great Barrington
          2.5 out of 5.0
           
           

          Situated in Great Barrington, this motel is within 3 mi (5 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and Ski Butternut. W.E.B. Du Bois Boyhood ...

          Travelodge by Wyndham Great Barrington Berkshires

          Travelodge by Wyndham Great Barrington Berkshires

          400 Stockbridge Rd, Great Barrington
            2.0 out of 5.0
             
             

            Situated in Great Barrington, this motel is within 6 mi (10 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and Ski Butternut. Mission House and ...

            Travelodge by Wyndham Great Barrington Berkshires$67

            Travelodge by Wyndham Great Barrington Berkshires$67
            Monument Mountain Motel

            Monument Mountain Motel

            247 Stockbridge Rd, Great Barrington
              2.5 out of 5.0
               
               

              Situated in Great Barrington, this motel is within 3 mi (5 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and Ski Butternut. W.E.B. Du Bois Boyhood ...

              The Windflower Inn

              The Windflower Inn

              684 South Egremont Road, Great Barrington
                3.0 out of 5.0
                 
                 

                Situated in Great Barrington, this bed & breakfast is 1.1 mi (1.8 km) from W.E.B. Du Bois Boyhood Homesite and within 6 mi (10 km) of Mahaiwe Performing Arts ...

                Wainwright Inn

                Wainwright Inn

                518 South Main Street, Great Barrington
                  3.0 out of 5.0
                   
                   

                  Situated in the city center, this bed & breakfast is close to Mahaiwe Performing Arts Center, Lake Mansfield Park, and W.E.B. Du Bois Boyhood Homesite. Local ...

                  The Barrington

                  The Barrington

                  281 Main St., Level 3, Great Barrington
                    4.0 out of 5.0
                     
                     

                    Situated in Great Barrington, this bed & breakfast is within 1 mi (2 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. W.E.B. Du Bois Boyhood Homesite ...

                    Holiday Inn Express Hotel & Suites Great Barrington

                    Holiday Inn Express Hotel & Suites Great Barrington

                    415 Stockbridge Rd, Great Barrington
                      2.5 out of 5.0
                       
                       

                      Situated in Great Barrington, this hotel is within 6 mi (10 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and Mission House. Ski Butternut and ...

                      Holiday Inn Express Hotel & Suites Great Barrington$272

                      Holiday Inn Express Hotel & Suites Great Barrington$272

                      Top Flight Deals

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