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Prestonsburg Vacation Packages

Embark on a voyage of country music discovery, hike rugged trails and visit historic battle sites at this popular town in Eastern Kentucky.

Prestonsburg is an attractive small town in the foothills of the Appalachian Mountains. With mountainous scenery, outdoor recreation and a rich country music heritage, it has plenty of fun things to see and do.

Explore the Jenny Wiley State Resort Park. Hike along trails passing through Appalachian terrain. Rent a pontoon boat or canoe for a trip across the park’s 1,100-acre (445-hectare) Dewey Lake. Anglers will relish fishing for bluegill, largemouth, catfish and crappie. During the fall and winter, book your place on an elk-viewing tour. Be sure to bring your camera.

If you enjoy history, visit Middle Creek National Battlefield. During the Civil War a decisive battle was fought here that ended Confederate control of the region. Drive 10 miles (16 kilometers) south of Prestonsburg to see the Battle of Ivy Mountain Monument. The 14-foot (4.2-meter) granite obelisk marks the spot of a famous skirmish between four Union regiments and the heavily outnumbered Confederates.

In the evening, enjoy some of Prestonsburg’s cultural attractions. See a play, musical or comedy show at the Jenny Wiley Theater. There are also matinee productions for children at various times of the year. The Mountain Arts Center is home to the Kentucky Opry and occasionally hosts some of the area’s most famous country stars. Dwight Yoakam, Billy Ray Cyrus and Patty Loveless have all performed on its stage.

Prestonsburg is located on a road dubbed the Country Music Highway, so named because many county music stars were born in the area. Finish your trip by spending several days driving along the 144-mile (232-kilometer) road that meanders down Kentucky’s eastern border. Highway markers point to the hometowns of some of the genre’s most famous names. 

During your Prestonsburg road trip, stop by some of these places and listen to live bluegrass and county music. Go to Staffordsville for Mountain Homeplace, a working farm that dates back to the 1850s. In Paintsville, tour the family home of country music legend Loretta Lynn.


Top Hotel Deals

See all 27 Hotels in Prestonsburg

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£95
Hampton Inn Pikeville

Hampton Inn Pikeville

831 Hambley Blvd, Pikeville
4.7
of 5, from 34 reviews
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 Park and Mountain Arts Center are also within 32 mi (52 km).

£56
Comfort Suites

Comfort Suites

51 Hal Rogers Dr, Prestonsburg
4.2
of 5, from 43 reviews
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 House and East Kentucky Science Center and Planetarium are also within 3 mi (5 km).

£43
Super 8 Prestonsburg

Super 8 Prestonsburg

80 Shoppers Path, Prestonsburg
3.1
of 5, from 27 reviews
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 Battlefield are also within 3 mi (5 km).

£42
Quality Inn Prestonsburg

Quality Inn Prestonsburg

1887 Us Highway 23 N, Prestonsburg
4.2
of 5, from 23 reviews
2.5 out of 5.0

Located in the heart of Prestonsburg, this hotel is within 6 mi (10 km) of Mountain Arts Center, Archer Park, and Middle Creek National Battlefield. East Kentucky Science Center and Planetarium and Samuel May House are also within 6 mi (10 km).

£74
Holiday Inn Express Hotel & Suites Pikeville

Holiday Inn Express Hotel & Suites Pikeville

476 S. Mayo Trail, Pikeville
4.0
of 5, from 49 reviews
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 Interstate Park and Mountain Arts Center are also within 32 mi (52 km).

£86
Ramada Paintsville Hotel and Conference Center

Ramada Paintsville Hotel and Conference Center

624 James Trimble Blvd, Paintsville
3.8
of 5, from 25 reviews
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 Lake State Park and Mountain HomePlace are also within 6 mi (10 km).

£35
Daniel Boone Motor Inn

Daniel Boone Motor Inn

150 Weddington Branch Road, Pikeville
2.4
of 5, from 8 reviews
2.5 out of 5.0

Situated in Pikeville, 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 Arts Center and Archer Park are also within 25 mi (40 km).

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