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

Madison Vacations

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

Hotwire can help you find your travel bliss with Madison 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 Madison

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 Madison 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 Madison well.

Top Hotel Deals

See all 229 Hotels in Madison
The Ebenezer House Bed & Breakfast

The Ebenezer House Bed & Breakfast

122 Seville Road, Madison
    3.0 out of 5.0
     
     

    Located in Swift Run Gap Entrance Shenandoah, this bed & breakfast is 6.1 mi (9.8 km) from Early Mountain Vineyards and within 12 mi (20 km) of Reynard Florence ...

    Cavalier Inn At The University of Virginia

    Cavalier Inn At The University of Virginia

    105 N. Emmet St, Charlottesville
      2.0 out of 5.0
       
       

      The hotel enjoys a quiet campus setting, a 15-minute drive from CHO Airport and 5 minutes from Charlottesville Amtrak Station. Art lovers can walk to the university's ...

      Country Inn & Suites by Radisson, Charlottesville-UVA, VA

      Country Inn & Suites by Radisson, Charlottesville-UVA, VA

      1600 Emmet Street, Charlottesville
        3.0 out of 5.0
         
         

        Situated in Charlottesville, this hotel is 0.9 mi (1.4 km) from Barracks Road Shopping Center and within 3 mi (5 km) of Rotunda and University of Virginia. Scott ...

        English Inn of Charlottesville

        English Inn of Charlottesville

        2000 Morton Drive, Charlottesville
          3.0 out of 5.0
           
           

          Situated in Charlottesville, this hotel is within 2 mi (3 km) of Barracks Road Shopping Center, Rotunda, and University of Virginia. Downtown Mall and Scott ...

          Mimslyn Inn Historic Hotels Of America

          Mimslyn Inn Historic Hotels Of America

          401 W Main St, Luray
            3.0 out of 5.0
             
             

            Located in Thorton Gap Entrance Shenandoah, this historic hotel is within 1 mi (2 km) of Warehouse Art Gallery and Luray Caverns. Car and Carriage Caravan Museum ...

            Mimslyn Inn Historic Hotels Of America$125

            Mimslyn Inn Historic Hotels Of America$125
            University of Virginia Inn at Darden

            University of Virginia Inn at Darden

            10 Duffy Boulevard, Charlottesville
              3.0 out of 5.0
               
               

              Situated in Charlottesville, this hotel is within a 15-minute walk of John Paul Jones Arena and University of Virginia. Rotunda and Scott Stadium are also within ...

              Omni Charlottesville Hotel

              Omni Charlottesville Hotel

              212 Ridge McIntire Rd, Charlottesville
                4.0 out of 5.0
                 
                 

                Omni Charlottesville Hotel is a 20-minute drive from Charlottesville Airport and walking distance from the eateries and boutiques at the Downtown Mall. For local ...

                DoubleTree by Hilton Hotel Charlottesville

                DoubleTree by Hilton Hotel Charlottesville

                990 Hilton Heights Rd, Charlottesville
                  3.5 out of 5.0
                   
                   

                  Situated near the airport, this hotel is 1.4 mi (2.3 km) from Fashion Square Mall and within 6 mi (10 km) of Rotunda and Downtown Mall. Scott Stadium and Virginia ...

                  Hyatt Place Charlottesville

                  Hyatt Place Charlottesville

                  2100 Bond Street, Charlottesville
                    3.0 out of 5.0
                     
                     

                    Situated in Charlottesville, this hotel is within 3 mi (5 km) of Barracks Road Shopping Center, Rotunda, and University of Virginia. Scott Stadium and Downtown ...

                    Hampton Inn Charlottesville

                    Hampton Inn Charlottesville

                    2035 India Rd, Charlottesville
                      2.5 out of 5.0
                       
                       

                      Situated in a shopping district, this hotel is within 3 mi (5 km) of Barracks Road Shopping Center, Rotunda, and University of Virginia. Downtown Mall and Scott ...

                      Top Flight Deals

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