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Southfield Vacations

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

Hotwire can help you find your travel bliss with Southfield 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 Southfield

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 Southfield 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 Southfield well.

Top Hotel Deals

See all 122 Hotels in Southfield
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
      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
        Days Inn by Wyndham Torrington

        Days Inn by Wyndham Torrington

        492 East Main St, Torrington
          2.0 out of 5.0
           
           

          Situated in Torrington, this motel is within 1 mi (2 km) of Hotchkiss-Fyler House Museum, KidsPlay Museum, and Warner Theater. Connecticut Valley Winery is 3 ...

          Days Inn by Wyndham Torrington$72

          Days Inn by Wyndham Torrington$72
          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
                Chambery Inn

                Chambery Inn

                199 Main St, Lee
                  3.0 out of 5.0
                   
                   

                  Situated in the mountains, this bed & breakfast is within a 5-minute walk of Animagic Museum of Animation and Lee Library. Greenock Country Club and Lee Prime ...

                  Interlaken Inn & Resort

                  Interlaken Inn & Resort

                  74 Interlaken Road, Lakeville
                    3.5 out of 5.0
                     
                     

                    Situated on a lake, this hotel is close to Holley-Williams House Museum and Scoville Memorial Library. Area attractions also include Lime Rock Park and Great ...

                    Rodeway Inn & Suites

                    Rodeway Inn & Suites

                    395 Winsted Rd, Torrington
                      2.5 out of 5.0
                       
                       

                      Situated in the historical district, this hotel is within 2 mi (3 km) of Hotchkiss-Fyler House Museum, KidsPlay Museum, and Warner Theater. Connecticut Valley ...

                      Rodeway Inn & Suites$78

                      Rodeway Inn & Suites$78

                      Top Flight Deals

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