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Jackson Vacations

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

Hotwire can help you find your travel bliss with Jackson 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 Jackson

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 Jackson 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 Jackson well.

Top Hotel Deals

See all 39 Hotels in Jackson
Jenny Wiley State Resort Park

Jenny Wiley State Resort Park

75 Theatre Ct, Prestonsburg
    2.5 out of 5.0
     
     

    Situated in Prestonsburg, this hotel is 0.1 mi (0.2 km) from Jenny Wiley State Resort Park and within 6 mi (10 km) of StoneCrest Golf Course and Archer Park. ...

    Natural Bridge State Resort Park

    Natural Bridge State Resort Park

    2135 Natural Bridge Road, Slade
      3.0 out of 5.0
       
       

      Situated in Slade, this cabin is 1.3 mi (2.1 km) from Natural Bridge State Park and 2.6 mi (4.1 km) from Kentucky Reptile Zoo. Red River Gorge is 10.7 mi (17.2 ...

      Super 8 by Wyndham Prestonsburg

      Super 8 by Wyndham Prestonsburg

      80 Shoppers Path, Prestonsburg
        2.0 out of 5.0
         
         

        Situated in the entertainment district, this hotel is within 1 mi (2 km) of Archer Park and Mountain Arts Center. Samuel May House and Middle Creek National ...

        Super 8 by Wyndham Prestonsburg$60

        Super 8 by Wyndham Prestonsburg$60
        Ramada Hotel & Conference Center by Wyndham Paintsville

        Ramada Hotel & Conference Center by Wyndham Paintsville

        624 James Trimble Blvd, Paintsville
          2.5 out of 5.0
           
           

          Situated in Paintsville, this hotel is 2.1 mi (3.4 km) from U.S. 23 Country Music Highway Museum and 2.3 mi (3.7 km) from Paintsville Golf Course. Paintsville ...

          Ramada Hotel & Conference Center by Wyndham Paintsville$99

          Ramada Hotel & Conference Center by Wyndham Paintsville$99
          Comfort Suites

          Comfort Suites

          51 Hal Rogers Dr, Prestonsburg
            2.5 out of 5.0
             
             

            Located in the heart of Prestonsburg, this hotel is within 1 mi (2 km) of Mountain Arts Center, Archer Park, and Middle Creek National Battlefield. Samuel May ...

            Comfort Suites$100

            Comfort Suites$100
            Campton Parkway Inn

            Campton Parkway Inn

            205 Quillins Chapel Service Rd., Campton
              2.0 out of 5.0
               
               

              Situated in the historical district, this motel is 9.9 mi (15.9 km) from Kentucky Reptile Zoo and within 20 mi (32 km) of Natural Bridge State Park and Red River ...

              Holiday Inn Express Hotel & Suites Hazard

              Holiday Inn Express Hotel & Suites Hazard

              192 Corporate Dr, Hazard
                2.5 out of 5.0
                 
                 

                Situated in the mountains, this hotel is 1.2 mi (2 km) from Hazard Village Shopping Center and 1.3 mi (2.1 km) from Hazard ARH Regional Medical Center. Hazard ...

                Holiday Inn Express Hotel & Suites Hazard$97

                Holiday Inn Express Hotel & Suites Hazard$97
                Brookshire Inn

                Brookshire Inn

                85 Hal Rogers Drive, Prestonsburg
                  2.5 out of 5.0
                   
                   

                  Situated in Prestonsburg, this hotel is within 2 mi (3 km) of Mountain Arts Center, Archer Park, and Middle Creek National Battlefield. Samuel May House and ...

                  Hampton Inn Suites Hazard

                  Hampton Inn Suites Hazard

                  70 Morton Blvd, Hazard
                     
                     

                    Located in the heart of Hazard, this hotel is within 2 mi (3 km) of Hazard ARH Regional Medical Center, Hazard Village Shopping Center, and Perry Park. Bobby ...

                    Cliffview Resort

                    Cliffview Resort

                    455 Cliffview Road, Campton
                      3.0 out of 5.0
                       
                       

                      Situated on a lake, this hotel is 7.6 mi (12.2 km) from Natural Bridge State Park and 9.8 mi (15.7 km) from Kentucky Reptile Zoo. Red River Gorge and Memory ...

                      Top Flight Deals

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