Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

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 286 Hotels in Chesterfield
Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

355 Chesterfield Ctr, Chesterfield
     
     

    Located in the heart of Chesterfield, this hotel is within 2 mi (3 km) of Westfield Chesterfield Mall, Sophia M. Sachs Butterfly House, and Faust Park. Taubman ...

    Hyatt Place St. Louis/Chesterfield

    Hyatt Place St. Louis/Chesterfield

    333 Chesterfield Center East, Chesterfield
      3.0 out of 5.0
       
       

      Situated in the business district, this hotel is within 2 mi (3 km) of Westfield Chesterfield Mall, Sophia M. Sachs Butterfly House, and Faust Park. Taubman ...

      Hyatt Place St. Louis/Chesterfield$99

      Hyatt Place St. Louis/Chesterfield$99
      Comfort Inn & Suites St. Louis - Chesterfield

      Comfort Inn & Suites St. Louis - Chesterfield

      18375 Chesterfield Arpt Rd, Chesterfield
        2.5 out of 5.0
         
         

        Located in the heart of Chesterfield, this hotel is 0.6 mi (0.9 km) from St. Louis Premium Outlets and within 6 mi (10 km) of Missouri Bluffs Golf Course and ...

        Comfort Inn & Suites St. Louis - Chesterfield$89

        Comfort Inn & Suites St. Louis - Chesterfield$89
        Homewood Suites by Hilton St. Louis-Chesterfield

        Homewood Suites by Hilton St. Louis-Chesterfield

        840 North Chesterfield Pkwy West, Chesterfield
          3.0 out of 5.0
           
           

          Situated in the business district, this hotel is within 1 mi (2 km) of Sophia M. Sachs Butterfly House and Faust Park. Westfield Chesterfield Mall is 1.4 mi ...

          Homewood Suites by Hilton St. Louis-Chesterfield$101

          Homewood Suites by Hilton St. Louis-Chesterfield$101
          Sonesta ES Suites St. Louis - Chesterfield

          Sonesta ES Suites St. Louis - Chesterfield

          15431 Conway Rd, Chesterfield
            3.0 out of 5.0
             
             

            Situated in the suburbs, this aparthotel is within 2 mi (3 km) of Sophia M. Sachs Butterfly House, Westfield Chesterfield Mall, and Faust Park. Myseum and Taubman ...

            Sonesta ES Suites St. Louis - Chesterfield$99

            Sonesta ES Suites St. Louis - Chesterfield$99
            SpringHill Suites by Marriott St. Louis Chesterfield

            SpringHill Suites by Marriott St. Louis Chesterfield

            1065 Chesterfield Pkwy E, Chesterfield
              3.0 out of 5.0
               
               

              Situated in the suburbs, this hotel is within 2 mi (3 km) of Sophia M. Sachs Butterfly House, Westfield Chesterfield Mall, and Faust Park. Myseum and Taubman ...

              SpringHill Suites by Marriott St. Louis Chesterfield$93

              SpringHill Suites by Marriott St. Louis Chesterfield$93
              Hampton Inn St. Louis/Chesterfield

              Hampton Inn St. Louis/Chesterfield

              16201 Swingley Ridge Road, Chesterfield
                3.5 out of 5.0
                 
                 

                Situated near the airport, this hotel is within 1 mi (2 km) of Westfield Chesterfield Mall and Sophia M. Sachs Butterfly House. Faust Park is 1.5 mi (2.3 km) ...

                Hampton Inn St. Louis/Chesterfield$101

                Hampton Inn St. Louis/Chesterfield$101
                Courtyard by Marriott St. Louis Chesterfield

                Courtyard by Marriott St. Louis Chesterfield

                17369 Chesterfield Airport Road, Chesterfield
                  3.0 out of 5.0
                   
                   

                  Situated in Chesterfield, this hotel is 1.3 mi (2.1 km) from Taubman Prestige Outlets and within 6 mi (10 km) of St. Louis Premium Outlets and Westfield Chesterfield ...

                  Courtyard by Marriott St. Louis Chesterfield$88

                  Courtyard by Marriott St. Louis Chesterfield$88
                  Hilton Garden Inn Chesterfield

                  Hilton Garden Inn Chesterfield

                  16631 Chesterfield Grove Ct, Chesterfield
                    3.0 out of 5.0
                     
                     

                    Situated in Chesterfield, this hotel is within 3 mi (5 km) of Westfield Chesterfield Mall, Taubman Prestige Outlets, and Sophia M. Sachs Butterfly House. Faust ...

                    Hilton Garden Inn Chesterfield$87

                    Hilton Garden Inn Chesterfield$87
                    DoubleTree by Hilton Hotel St. Louis - Chesterfield

                    DoubleTree by Hilton Hotel St. Louis - Chesterfield

                    16625 Swingley Ridge Rd, Chesterfield
                      3.5 out of 5.0
                       
                       

                      Situated in the suburbs, this hotel is 1.1 mi (1.8 km) from Westfield Chesterfield Mall and within 3 mi (5 km) of Sophia M. Sachs Butterfly House and Faust Park. ...

                      DoubleTree by Hilton Hotel St. Louis - Chesterfield$118

                      DoubleTree by Hilton Hotel St. Louis - Chesterfield$118

                      Top Flight Deals

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