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Highland Vacations

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

Hotwire can help you find your travel bliss with Highland 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 Highland

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 Highland 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 Highland well.

Top Hotel Deals

See all 56 Hotels in Highland
Baymont by Wyndham Highland

Baymont by Wyndham Highland

20 Central Blvd, Highland
    3.0 out of 5.0
     
     

    Situated in a rural location, this hotel is 11.1 mi (17.9 km) from Copper Dock Winery and within 20 mi (32 km) of McKendree University and St. Andrew's Episcopal ...

    Baymont by Wyndham Highland$96

    Baymont by Wyndham Highland$96
    The Tibbetts House

    The Tibbetts House

    801 9th St, Highland
      3.0 out of 5.0
       
       

      Situated in Highland, this bed & breakfast is 11.4 mi (18.3 km) from Copper Dock Winery and within 20 mi (32 km) of McKendree University and St. Andrew's Episcopal ...

      The Tibbetts House$130

      The Tibbetts House$130
      Home Towne Suites - O'Fallon

      Home Towne Suites - O'Fallon

      148 Regency Park, O'Fallon
        2.0 out of 5.0
         
         

        Situated in the suburbs, this hotel is close to St. Claire Square Mall and Far Oaks Golf Course. Area attractions also include Stonewolf Golf Course and Pleasant ...

        Home Towne Suites - O'Fallon$54

        Home Towne Suites - O'Fallon$54
        Drury Inn & Suites St. Louis Fairview Heights

        Drury Inn & Suites St. Louis Fairview Heights

        12 Ludwig Dr, Fairview Heights
          3.0 out of 5.0
           
           

          Located in the heart of Fairview Heights, this hotel is 0.7 mi (1.1 km) from St. Claire Square Mall and within 3 mi (5 km) of Stonewolf Golf Course and Pleasant ...

          Drury Inn & Suites St. Louis Fairview Heights$105

          Drury Inn & Suites St. Louis Fairview Heights$105
          Baymont by Wyndham O'Fallon St. Louis Area

          Baymont by Wyndham O'Fallon St. Louis Area

          1320 Park Plaza Drive, O'Fallon
            2.0 out of 5.0
             
             

            Situated in the suburbs, this hotel is 7.5 mi (12 km) from Scott Air Force Base and 12 mi (19.3 km) from Fairmount Park Racetrack. Gateway Arch and Busch Stadium ...

            Baymont by Wyndham O'Fallon St. Louis Area$63

            Baymont by Wyndham O'Fallon St. Louis Area$63
            La Quinta Inn & Suites O'Fallon, IL - St. Louis

            La Quinta Inn & Suites O'Fallon, IL - St. Louis

            136 Regency Park, O'Fallon
              2.5 out of 5.0
               
               

              Situated in O'Fallon, this hotel is 2.9 mi (4.6 km) from St. Claire Square Mall and within 6 mi (10 km) of Far Oaks Golf Course and Stonewolf Golf Course. Southwestern ...

              La Quinta Inn & Suites O'Fallon, IL - St. Louis$88

              La Quinta Inn & Suites O'Fallon, IL - St. Louis$88
              La Quinta Inn & Suites Collinsville

              La Quinta Inn & Suites Collinsville

              6 Gateway Dr, Collinsville
                2.5 out of 5.0
                 
                 

                Situated in the city center, this hotel is close to Gateway Conference Center, Splash City Family Waterpark, and Gateway Fun Park. Local attractions also include ...

                La Quinta Inn & Suites Collinsville$63

                La Quinta Inn & Suites Collinsville$63
                Comfort Suites Fairview Heights

                Comfort Suites Fairview Heights

                137 Ludwig Dr, Fairview Heights
                  2.5 out of 5.0
                   
                   

                  Situated in the city center, this hotel is close to St. Claire Square Mall, Pleasant Ridge Park, and Stonewolf Golf Course. Local attractions also include Far ...

                  Comfort Suites Fairview Heights$94

                  Comfort Suites Fairview Heights$94
                  Best Western Plus Mascoutah/SAFB

                  Best Western Plus Mascoutah/SAFB

                  9730 Hayden Drive, Mascoutah
                    2.5 out of 5.0
                     
                     

                    Situated in Mascoutah, this hotel is in the same area as Scott Air Force Base and McKendree University. Regional attractions also include Southwestern Illinois ...

                    Best Western Plus Mascoutah/SAFB$83

                    Best Western Plus Mascoutah/SAFB$83
                    Country Inn & Suites by Radisson, O'Fallon, IL

                    Country Inn & Suites by Radisson, O'Fallon, IL

                    116 Regency Park, O'Fallon
                      3.0 out of 5.0
                       
                       

                      Situated in O'Fallon, this hotel is 2.7 mi (4.4 km) from St. Claire Square Mall and within 6 mi (10 km) of Far Oaks Golf Course and Stonewolf Golf Course. Pleasant ...

                      Country Inn & Suites by Radisson, O'Fallon, IL$71

                      Country Inn & Suites by Radisson, O'Fallon, IL$71

                      Top Flight Deals

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