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Prestonsburg Vacations

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

Hotwire can help you find your travel bliss with Prestonsburg 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 Prestonsburg

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 Prestonsburg 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 Prestonsburg well.

Top Hotel Deals

See all 26 Hotels in Prestonsburg
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. ...

    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
          Holiday Inn Express Hotel & Suites Pikeville

          Holiday Inn Express Hotel & Suites Pikeville

          476 S. Mayo Trail, Pikeville
            2.5 out of 5.0
             
             

            Situated in a rural location, this hotel is 1.6 mi (2.6 km) from University of Pikeville and 1.7 mi (2.8 km) from Eastern Kentucky Exposition Center. Breaks ...

            Holiday Inn Express Hotel & Suites Pikeville$100

            Holiday Inn Express Hotel & Suites Pikeville$100
            The Landmark Hotel

            The Landmark Hotel

            190 S Mayo Trail, Pikeville
              3.5 out of 5.0
               
               

              Situated in Pikeville, this hotel is within 1 mi (2 km) of University of Pikeville and Eastern Kentucky Exposition Center. Breaks Interstate Park and Mountain ...

              Daniel Boone Motor Inn

              Daniel Boone Motor Inn

              150 Weddington Branch Road, Pikeville
                2.5 out of 5.0
                 
                 

                Situated in Coal Run Village, this motel is 6.3 mi (10.1 km) from University of Pikeville and 6.4 mi (10.3 km) from Eastern Kentucky Exposition Center. Mountain ...

                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 ...

                  Brookshire Inn & Suites

                  Brookshire Inn & Suites

                  123 Alexandra Drive, Pikeville
                    2.5 out of 5.0
                     
                     

                    Situated in Pikeville, this hotel is 3.8 mi (6.1 km) from University of Pikeville and 3.9 mi (6.3 km) from Eastern Kentucky Exposition Center. Mountain Arts ...

                    Hampton Inn Pikeville

                    Hampton Inn Pikeville

                    831 Hambley Blvd, Pikeville
                      2.5 out of 5.0
                       
                       

                      Located in the heart of Pikeville, this hotel is within a 5-minute walk of University of Pikeville and Eastern Kentucky Exposition Center. Breaks Interstate ...

                      Hampton Inn Pikeville$124

                      Hampton Inn Pikeville$124