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Sheffield Vacations

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

Hotwire can help you find your travel bliss with Sheffield 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 Sheffield

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 Sheffield 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 Sheffield well.

Top Hotel Deals

See all 135 Hotels in Sheffield
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
    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
      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
        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
            Cranwell Spa and Golf Resort

            Cranwell Spa and Golf Resort

            55 Lee Road, Lenox
              3.5 out of 5.0
               
               

              Situated in Lenox, this spa resort is within 2 mi (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum, and Lenox Library. Shakespeare and Company ...

              Cranwell Spa and Golf Resort$139

              Cranwell Spa and Golf Resort$139
              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 ...

                Berkshire Mountain Lodge$150

                Berkshire Mountain Lodge$150
                Black Swan Inn, an Ascend Collection Hotel

                Black Swan Inn, an Ascend Collection Hotel

                435 Laurel St, Lee
                  3.0 out of 5.0
                   
                   

                  Situated on a lake, this hotel is within 1 mi (2 km) of Animagic Museum of Animation and Lee Library. Greenock Country Club and The Mount are also within 3 mi ...

                  Black Swan Inn, an Ascend Collection Hotel$95

                  Black Swan Inn, an Ascend Collection Hotel$95
                  Pleasant Valley Motel West Stockbridge

                  Pleasant Valley Motel West Stockbridge

                  42 Stockbridge Rd, West Stockbridge
                    2.0 out of 5.0
                     
                     

                    Situated near the beach, this motel is 2.4 mi (3.8 km) from Berkshire Botanical Garden and within 6 mi (10 km) of Norman Rockwell Museum and Naumkeag. National ...

                    Pleasant Valley Motel West Stockbridge$43

                    Pleasant Valley Motel West Stockbridge$43
                    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

                      Top Flight Deals

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