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Chesterfield Vacations

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

Hotwire can help you find your travel bliss with Chesterfield 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 Chesterfield

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 Chesterfield 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 Chesterfield well.

Top Hotel Deals

See all 93 Properties in Chesterfield
Hampton Inn and Suites Detroit/Chesterfield Township

Hampton Inn and Suites Detroit/Chesterfield Township

45725 Marketplace Blvd, Chesterfield
    2.5 out of 5.0
     
     

    Situated in Chesterfield, this hotel is 6 mi (9.7 km) from Metro Beach and within 12 mi (20 km) of Lakeside Mall and Freedom Hill Amphitheatre. Pine Valley Golf ...

    Hampton Inn and Suites Detroit/Chesterfield Township$97

    Hampton Inn and Suites Detroit/Chesterfield Township$97
    Holiday Inn Express & Suites Chesterfield

    Holiday Inn Express & Suites Chesterfield

    45825 Marketplace Blvd, Chesterfield
      2.5 out of 5.0
       
       

      Situated in Chesterfield, this hotel is 6.1 mi (9.8 km) from Metro Beach and within 12 mi (20 km) of Lakeside Mall and Freedom Hill Amphitheatre. Detroit Zoo ...

      Holiday Inn Express & Suites Chesterfield$95

      Holiday Inn Express & Suites Chesterfield$95
      Fairfield Inn & Suites by Marriott Detroit Chesterfield

      Fairfield Inn & Suites by Marriott Detroit Chesterfield

      45800 Market Place Blvd, Chesterfield
        2.5 out of 5.0
         
         

        Situated in Chesterfield, this hotel is within 12 mi (20 km) of Metro Beach, Lakeside Mall, and Freedom Hill Amphitheatre. Pine Valley Golf Course and Somerset ...

        Fairfield Inn & Suites by Marriott Detroit Chesterfield$98

        Fairfield Inn & Suites by Marriott Detroit Chesterfield$98
        Red Roof Inn Detroit - Royal Oak Madison Heights

        Red Roof Inn Detroit - Royal Oak Madison Heights

        32511 Concord Drive, Madison Heights
          2.0 out of 5.0
           
           

          Situated in Madison Heights, this hotel is 1.7 mi (2.8 km) from Red Oaks Waterpark and within 6 mi (10 km) of Troy Historic Village and Royal Oak Music Theatre. ...

          Red Roof Inn Detroit - Royal Oak Madison Heights$55

          Red Roof Inn Detroit - Royal Oak Madison Heights$55
          Days Inn & Suites by Wyndham Rochester Hills MI

          Days Inn & Suites by Wyndham Rochester Hills MI

          1919 Star Batt Dr., Rochester Hills
            2.5 out of 5.0
             
             

            Situated in Rochester Hills, this hotel is within 6 mi (10 km) of Meadow Brook Amphitheatre, Oakland University, and Chrysler LLC Headquarters. Palace of Auburn ...

            Days Inn & Suites by Wyndham Rochester Hills MI$55

            Days Inn & Suites by Wyndham Rochester Hills MI$55
            Red Roof Inn Detroit - St Clair Shores

            Red Roof Inn Detroit - St Clair Shores

            31800 Little Mack Rd, Roseville
              2.0 out of 5.0
               
               

              Situated in Roseville, this hotel is within 9 mi (15 km) of Macomb Music Theatre, Metro Beach, and Freedom Hill Amphitheatre. Red Oaks Waterpark and Harpos Concert ...

              Red Roof Inn Detroit - St Clair Shores$56

              Red Roof Inn Detroit - St Clair Shores$56
              Red Roof Inn Detroit - Warren

              Red Roof Inn Detroit - Warren

              26300 Dequindre Rd, Warren
                2.0 out of 5.0
                 
                 

                Located in the heart of Warren, this hotel is 2.8 mi (4.5 km) from Red Oaks Waterpark and within 6 mi (10 km) of Detroit Zoo and Royal Oak Music Theatre. Oakland ...

                Red Roof Inn Detroit - Warren$54

                Red Roof Inn Detroit - Warren$54
                Comfort Inn Utica

                Comfort Inn Utica

                11401 Hall Rd, Utica
                  2.5 out of 5.0
                   
                   

                  Situated in the business district, this hotel is 2.5 mi (4 km) from Lakeside Mall and within 9 mi (15 km) of Freedom Hill Amphitheatre and Macomb Music Theatre. ...

                  Comfort Inn Utica$70

                  Comfort Inn Utica$70
                  Wyndham Garden Sterling Heights

                  Wyndham Garden Sterling Heights

                  34911 Van Dyke Ave, Sterling Heights
                    3.0 out of 5.0
                     
                     

                    Set in Sterling Heights, this family-friendly hotel is within 12 mi (20 km) of Lakeside Mall, Somerset Collection, and Metro Beach. Royal Oak Music Theatre and ...

                    Wyndham Garden Sterling Heights$91

                    Wyndham Garden Sterling Heights$91
                    Red Roof Inn Detroit - Troy

                    Red Roof Inn Detroit - Troy

                    2350 Rochester Court, Troy
                      2.0 out of 5.0
                       
                       

                      Situated in Troy, this hotel is 2.5 mi (4.1 km) from Troy Historic Village and within 6 mi (10 km) of Somerset Collection and Red Oaks Waterpark. Detroit Zoo ...

                      Red Roof Inn Detroit - Troy$51

                      Red Roof Inn Detroit - Troy$51

                      Top Flight Deals

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