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Chester Vacations

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

Hotwire can help you find your travel bliss with Chester 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 Chester

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 Chester 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 Chester well.

Top Hotel Deals

See all 24 Properties in Chester
Best Western Chester Hotel

Best Western Chester Hotel

2150 State Street, Chester
    2.5 out of 5.0
     
     

    Situated in Chester, this hotel is 0.7 mi (1.1 km) from Chester Skating Rink and 2.1 mi (3.3 km) from Elzie C. Segar Memorial Park. Mary's River Covered Bridge ...

    Best Western Chester Hotel$90

    Best Western Chester Hotel$90
    Sparta Motel

    Sparta Motel

    700 South Saint Louis Street, Sparta
      2.0 out of 5.0
       
       

      Situated in Sparta, this motel is within 1 mi (2 km) of Misselhorn Art Gallery and Sparta Country Club. Mary's River Covered Bridge and Chester Skating Rink ...

      Sparta Motel$50

      Sparta Motel$50
      Briarwood Inn of Sparta

      Briarwood Inn of Sparta

      1755 North Market Street, Sparta
        2.5 out of 5.0
         
         

        Situated in Sparta, this motel is 2.1 mi (3.4 km) from Misselhorn Art Gallery and 3 mi (4.8 km) from Sparta Country Club. Mary's River Covered Bridge and Chester ...

        Briarwood Inn of Sparta$69

        Briarwood Inn of Sparta$69
        Holiday Inn Express Hotel & Suites Sparta

        Holiday Inn Express Hotel & Suites Sparta

        1301 N Market St, Sparta
          2.5 out of 5.0
           
           

          Situated in a rural location, this hotel is 1.6 mi (2.5 km) from Misselhorn Art Gallery and 2.4 mi (3.9 km) from Sparta Country Club. Fort Kaskaskia is 20 mi ...

          Holiday Inn Express Hotel & Suites Sparta$115

          Holiday Inn Express Hotel & Suites Sparta$115
          Budget Inn - Sparta

          Budget Inn - Sparta

          402 E Broadway St, Sparta
            2.5 out of 5.0
             
             

            Situated in Sparta, this motel is 0.8 mi (1.3 km) from Misselhorn Art Gallery and 1.6 mi (2.6 km) from Sparta Country Club. Mary's River Covered Bridge and Chester ...

            K-River Motel & Campground

            K-River Motel & Campground

            7797 Route 154, Baldwin
              2.0 out of 5.0
               
               

              Situated in Baldwin, this motel is 10 mi (16.1 km) from Misselhorn Art Gallery and 10.4 mi (16.7 km) from Sparta Country Club. Fort Kaskaskia and Chester Skating ...

              K-River Motel & Campground$64

              K-River Motel & Campground$64
              Americas Best Value Inn & Suites-Pinckneyville

              Americas Best Value Inn & Suites-Pinckneyville

              5700 Illinois Route 154, Pinckneyville
                2.0 out of 5.0
                 
                 

                Situated in Pinckneyville, this hotel is 4.2 mi (6.8 km) from Pinckneyville Fairgrounds and 7.4 mi (12 km) from Pyramid State Park. DuQuoin State Fairgrounds ...

                Americas Best Value Inn & Suites-Pinckneyville$68

                Americas Best Value Inn & Suites-Pinckneyville$68
                Quality Inn

                Quality Inn

                1200 W Gannon Dr, Festus
                  3.0 out of 5.0
                   
                   

                  Located in the business district, this family-friendly hotel is within 20 mi (32 km) of Mastodon State Historic Site, Sunridge Park, and Persimmon Ridge Winery. ...

                  Quality Inn$76

                  Quality Inn$76
                  Super 8 by Wyndham Perryville

                  Super 8 by Wyndham Perryville

                  1119 Vincent Dr, Perryville
                    2.0 out of 5.0
                     
                     

                    Situated in Perryville, this motel is 0.9 mi (1.5 km) from Perryville Country Club and 1.7 mi (2.8 km) from National Shrine of Our Lady of the Miraculous Medal. ...

                    Super 8 by Wyndham Perryville$77

                    Super 8 by Wyndham Perryville$77
                    Microtel Inn & Suites by Wyndham Sainte Genevieve

                    Microtel Inn & Suites by Wyndham Sainte Genevieve

                    21958 Hwy 32, Ste Genevieve
                      2.0 out of 5.0
                       
                       

                      Located in the heart of Ste Genevieve, this hotel is within 32 mi (52 km) of Elzie C. Segar Memorial Park, Chester Skating Rink, and Perryville Country Club. ...

                      Microtel Inn & Suites by Wyndham Sainte Genevieve$67

                      Microtel Inn & Suites by Wyndham Sainte Genevieve$67

                      Top Flight Deals

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