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Monticello Vacations

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

Hotwire can help you find your travel bliss with Monticello 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 Monticello

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 Monticello 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 Monticello well.

Top Hotel Deals

See all 61 Hotels in Monticello
Best Western Lake Cumberland Inn

Best Western Lake Cumberland Inn

2030 E Highway 90, Monticello
    2.5 out of 5.0
     
     

    Situated in Monticello, this hotel is 2.6 mi (4.2 km) from Wayne County Historical Museum and 7.7 mi (12.3 km) from Lake Cumberland Winery. Burnside Marina and ...

    Best Western Lake Cumberland Inn$115

    Best Western Lake Cumberland Inn$115
    IndianSummer LakeHouse

    IndianSummer LakeHouse

    8161 West Highway 92, Monticello
      2.0 out of 5.0
       
       

      Situated in Monticello, this bed & breakfast is 8.3 mi (13.4 km) from Wayne County Historical Museum and within 32 mi (52 km) of Lake Cumberland Winery and Burnside ...

      Monticello Motel

      Monticello Motel

      180 N Main St, Monticello
        2.5 out of 5.0
         
         

        Situated in Monticello, this motel is 0.1 mi (0.2 km) from Wayne County Historical Museum and 9.3 mi (15 km) from Lake Cumberland Winery. Burnside Marina and ...

        Cumberland Falls State Resort Park

        Cumberland Falls State Resort Park

        7351 Hwy. 90, Corbin
          2.5 out of 5.0
           
           

          Situated in Corbin, this hotel is 0.6 mi (0.9 km) from Cumberland Falls and within 20 mi (32 km) of The Arena at SE KY Agricultural and Expo Complex and Somerset ...

          Red Roof Inn Whitley City 

          Red Roof Inn Whitley City 

          1116 N Highway 27, Whitley City
            2.0 out of 5.0
             
             

            Situated in a rural location, this hotel is 1.6 mi (2.7 km) from Somerset Community College and 11.1 mi (17.9 km) from Split Bow Arch Overlook. Cumberland Falls ...

            Red Roof Inn Somerset

            Red Roof Inn Somerset

            1201 S Highway 27, Somerset
              2.0 out of 5.0
               
               

              Situated near the airport, this motel is 1.2 mi (1.9 km) from The Center For Rural Development and within 3 mi (5 km) of Somerset Community College and SomerSplash. ...

              Red Roof Inn Somerset$67

              Red Roof Inn Somerset$67
              Courtyard by Marriott Somerset

              Courtyard by Marriott Somerset

              2254 South Highway 27, Somerset
                3.0 out of 5.0
                 
                 

                Situated in Somerset, this hotel is within a 10-minute walk of The Center For Rural Development and Somerset Community College. Waitsboro Hills Golf Course is ...

                Courtyard by Marriott Somerset$129

                Courtyard by Marriott Somerset$129
                Lake Cumberland State Resort Park

                Lake Cumberland State Resort Park

                5465 State Park Rd, Jamestown
                  2.5 out of 5.0
                   
                   

                  Situated in Jamestown, this hotel is 0.7 mi (1.2 km) from Lake Cumberland State Resort Park and 8.5 mi (13.7 km) from Wolf Creek National Fish Hatchery. Lake ...

                  Quality Inn & Suites Somerset

                  Quality Inn & Suites Somerset

                  240 N Highway 27, Somerset
                    2.5 out of 5.0
                     
                     

                    Located in the heart of Somerset, this hotel is 2.4 mi (3.9 km) from SomerSplash and within 9 mi (15 km) of The Center For Rural Development and Somerset Community ...

                    Country Inn & Suites by Radisson, Somerset, KY

                    Country Inn & Suites by Radisson, Somerset, KY

                    515 N Hwy 27, Somerset
                      2.5 out of 5.0
                       
                       

                      Situated in Somerset, this hotel is 1.2 mi (1.9 km) from SomerSplash and within 6 mi (10 km) of The Center For Rural Development and Somerset Community College. ...

                      Country Inn & Suites by Radisson, Somerset, KY$64

                      Country Inn & Suites by Radisson, Somerset, KY$64

                      Top Flight Deals

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