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Middlefield Vacations

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

Hotwire can help you find your travel bliss with Middlefield 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 Middlefield

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 Middlefield 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 Middlefield well.

Top Hotel Deals

See all 128 Hotels in Middlefield
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$105

    Vacation Village in the Berkshires$105
    Jiminy Peak Mountain Resort

    Jiminy Peak Mountain Resort

    37 Corey Rd, Hancock
      3.0 out of 5.0
       
       

      Located in the mountains, this Hancock condo resort offering ski-in/ski-out access is 6.1 mi (9.8 km) from Mount Greylock State Reservation Visitor Center and ...

      Jiminy Peak Mountain Resort$115

      Jiminy Peak Mountain Resort$115
      Fairfield Inn & Suites Springfield Northampton/Amherst

      Fairfield Inn & Suites Springfield Northampton/Amherst

      115A Conz Street, Northampton
        3.0 out of 5.0
         
         

        Located in the heart of Northampton, this hotel is within a 15-minute walk of Academy of Music Theater and Calvin Theater. Smith College and Smith College Botanic ...

        Fairfield Inn & Suites Springfield Northampton/Amherst$116

        Fairfield Inn & Suites Springfield Northampton/Amherst$116
        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$72

          Yankee Inn$72
          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$114

            Courtyard by Marriott Lenox Berkshires$114
            Hotel Northampton

            Hotel Northampton

            36 King Street, Northampton
              3.5 out of 5.0
               
               

              Located in the heart of Northampton, this historic hotel is within a 10-minute walk of Calvin Theater, Academy of Music Theater, and Smith College. Smith College ...

              Hampton Inn & Suites Berkshires Lenox

              Hampton Inn & Suites Berkshires Lenox

              445 Pittsfield Rd, Lenox
                2.5 out of 5.0
                 
                 

                Situated in a rural location, this hotel is within 2 mi (3 km) of Arrowhead Museum, Kennedy Park, and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary ...

                Hampton Inn & Suites Berkshires Lenox$101

                Hampton Inn & Suites Berkshires Lenox$101
                Best Western Plus Berkshire Hills Inn & Suites

                Best Western Plus Berkshire Hills Inn & Suites

                1350 W Housatonic St, Pittsfield
                  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 ...

                  Best Western Plus Berkshire Hills Inn & Suites$87

                  Best Western Plus Berkshire Hills Inn & Suites$87
                  Quality Inn & Suites Northampton-Amherst

                  Quality Inn & Suites Northampton-Amherst

                  117 Conz St, Northampton
                    2.5 out of 5.0
                     
                     

                    Situated in the entertainment district, this hotel is within a 15-minute walk of Calvin Theater and Academy of Music Theater. Smith College and Smith College ...

                    Quality Inn & Suites Northampton-Amherst$89

                    Quality Inn & Suites Northampton-Amherst$89
                    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

                      Top Flight Deals

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