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.

Madison Flight + Hotel packages

Top Hotel Deals

See all 65 Hotels in Madison
The Lost Pearl

The Lost Pearl

4194 Dayton Rd., Madison
    3.5 out of 5.0
     
     

    Situated in Madison, this romantic bed & breakfast is within 6 mi (10 km) of Grand River Cellars Winery, St. Joseph Vineyards, and The Winery at Spring Hill. ...

    SkyLight Inn Cleveland - Willoughby

    SkyLight Inn Cleveland - Willoughby

    34600 Maplegrove Rd, Willoughby
      2.5 out of 5.0
       
       

      Situated in Willoughby, this motel is 2.7 mi (4.3 km) from Classic Park and within 6 mi (10 km) of Indian Museum of Lake County and North Chagrin Reservation. ...

      SkyLight Inn Cleveland - Willoughby$46

      SkyLight Inn Cleveland - Willoughby$46
      Red Roof Inn Cleveland East - Willoughby

      Red Roof Inn Cleveland East - Willoughby

      4166 State Route 306, Willoughby
        2.0 out of 5.0
         
         

        Located in the heart of Willoughby, this hotel is within 9 mi (15 km) of Classic Park, Lake Metroparks Farmpark, and Mentor Civic Arena. North Chagrin Reservation ...

        Red Roof Inn Cleveland East - Willoughby$57

        Red Roof Inn Cleveland East - Willoughby$57
        Quail Hollow Resort Trademark Collection by Wyndham

        Quail Hollow Resort Trademark Collection by Wyndham

        11080 Concord-Hambden Rd, Painesville
          3.5 out of 5.0
           
           

          Located in Painesville, this family-friendly hotel is 2.7 mi (4.3 km) from Little Mountain Country Club, and within 6 mi (10 km) of Lake County History Center ...

          Quail Hollow Resort Trademark Collection by Wyndham$63

          Quail Hollow Resort Trademark Collection by Wyndham$63
          Punderson Manor Lodge and Conference Center

          Punderson Manor Lodge and Conference Center

          11755 Kinsman Rd, Newbury
            3.5 out of 5.0
             
             

            Located on the waterfront, this family-friendly hotel is 0.3 mi (0.5 km) from Punderson State Park and 7.5 mi (12 km) from Alpine Valley. Legacy Village and ...

            Punderson Manor Lodge and Conference Center$108

            Punderson Manor Lodge and Conference Center$108
            Americas Best Value Inn Austinburg

            Americas Best Value Inn Austinburg

            2352 State Route 45 N, Austinburg
              2.0 out of 5.0
               
               

              Located in the heart of Austinburg, this motel is within 1 mi (2 km) of Austinburg Township Park and Maple Ridge Golf Course. Harpersfield Covered Bridge and ...

              Americas Best Value Inn Austinburg$59

              Americas Best Value Inn Austinburg$59
              Best Western Plus Lawnfield Inn & Suites

              Best Western Plus Lawnfield Inn & Suites

              8434 Mentor Avenue, Mentor
                3.0 out of 5.0
                 
                 

                Situated in Mentor, this hotel is 0.6 mi (1 km) from James Garfield National Historic Site and 2.7 mi (4.3 km) from Mentor Civic Arena. Indian Museum of Lake ...

                Best Western Plus Lawnfield Inn & Suites$103

                Best Western Plus Lawnfield Inn & Suites$103
                Holiday Inn Cleveland Northeast - Mentor

                Holiday Inn Cleveland Northeast - Mentor

                7701 Reynolds Rd, Mentor
                  3.0 out of 5.0
                   
                   

                  Situated in the entertainment district, this hotel is 2.2 mi (3.5 km) from James Garfield National Historic Site and 2.6 mi (4.2 km) from Indian Museum of Lake ...

                  Holiday Inn Cleveland Northeast - Mentor$93

                  Holiday Inn Cleveland Northeast - Mentor$93
                  Motel 6 Cleveland-Willoughby

                  Motel 6 Cleveland-Willoughby

                  35110 Maplegrove Road, Willoughby
                    2.0 out of 5.0
                     
                     

                    Situated in Willoughby, this motel is 2.7 mi (4.3 km) from Classic Park and within 6 mi (10 km) of Indian Museum of Lake County and North Chagrin Reservation. ...

                    Motel 6 Cleveland-Willoughby$45

                    Motel 6 Cleveland-Willoughby$45
                    Hampton Inn Ashtabula

                    Hampton Inn Ashtabula

                    2900 GH Dr, Austinburg
                      2.5 out of 5.0
                       
                       

                      Situated in Austinburg, this hotel is 0.8 mi (1.3 km) from Austinburg Township Park and 1.5 mi (2.4 km) from Maple Ridge Golf Course. Harpersfield Covered Bridge ...

                      Hampton Inn Ashtabula$125

                      Hampton Inn Ashtabula$125

                      Top Flight Deals

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