Holiday houses in Harrodsburg

Pappy’s Roost (Old Town Vibe!)

Verified provider!! Pappy’s Roost is vintage and is up the street from a railroad track that has locomotives coming through very slowly because of the tight confines of Harrodsburg. The track is not extremely close, but you can definitely see the train when standing on the sidewalk in front of The Roost. The Roost still can offer sound sleep at night because the proximity is not near enough to the tracks to be startling or disturbing to sleep. Pappy’s has been restored and has every amenity!

The Luxe/ Hot Tub/ On Bright Leaf Golf Course

Nestled on the illustrious Bright Leaf Golf Course in the historic town of Harrodsburg, Kentucky, you'll find this charming two-bedroom, two-bathroom apartment. With a host of modern amenities, private deck, a communal fire pit, and more, your stay promises both comfort and convenience. This prime location is your gateway to easy exploration of the local area and visits to attractions like Shakertown, Old Fort Harrod State Park, the KY Bourbon Trail, Centre College, and many other destinations.

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

Hot Tub | 3 King Suites | Bourbon Trail

Enjoy an unforgettable stay at the Bluegrass & Bourbon Bungalow. With a hot tub, a spacious back deck, and a horse theme, this peaceful home is a perfect blend of modern comforts and vintage charm. Just a short distance from Fort Harrod and iconic distilleries, this is the ultimate getaway for bourbon enthusiasts. Shaker Village of Pleasant Hill - 11 min drive Fort Harrod State Park - 12 min drive Four Roses Distillery - 19 min drive Book For Lasting Memories In Harrodsburg—See Details Below

Paradise Cottage Enjoy lake Views and Lake Access!

Relax and enjoy! Great Herrington Lake views with lake access at Paradise Cottage! Peaceful private setting on one of the most beautiful parts of the lake. Located Mins from Multiple marinas, Bourbon trail, golf courses, Centre College/Asbury University events. 3 bedrooms, 5 beds, 2 full bathrooms, washer/dryer, newly remodeled. Sleeps 8. Includes: wi-fi, Hulu, 2 TVs, multiple decks, covered side patio, fire pit, gas grill, corn hole, kayaks and lily pad included with stay! Four parking spaces!

The Blue Cottage / Walk to Downtown Harrodsburg

Nestled amongst the site of Old Graham Springs is where you will find The Blue Cottage. Walking distance to Downtown Harrodsburg, this charming ranch home has been completely renovated & the owners spared no expense. Featuring 3 private bedrooms, 1 bath, hardwood floors, instgramable kitchen, and so much more! We are located 12 miles to Wilderness Trail Distillery, 1/2 mile to Haggin Hospital, 8 Miles to Shaker Village, and so much more. Enjoy staying in the oldest city West of the Appalachia

New Quiet Retreat Hot Tub Shaker Village Danville

Kick back and relax in this calm, stylish space. Brand new build featuring a spacious living room, 3 bedrooms with flat screen TVs, luxurious Primary bathroom with walk in closet. Kitchen fully stocked. Great outdoor space with Hot Tub. Central location, close to Danville, Harrodsburg and Lawrenceburg. A short drive to Shaker Village, Bright Leaf golf, Herrington Lake, within 30 miles of many distilleries on the bourbon trail, and Keeneland. Perfect spot to enjoy the beauty of Kentucky.

Charming Dog Friendly Farmhouse in Harrodsburg

Relax on the front porch of this fully updated country farmhouse near Harrodsburg, Kentucky. Beautiful views, country charm. Seven minutes to groceries, restaurants & historic Main Street. 15-20 minute drive to Danville, Ky. Local areas of interest include Old Fort Harrod State Park, Shaker Village, Kentucky Bourbon Trail, Centre College, distilleries and wineries. Quaint little town that is within an hour to 1.5 hours of Lexington & Louisville. Your hosts are only a stones throw away.

Bourbon Villa at Daynabrook Farm, Hot Tub-3

Keep it simple and escape to the rolling bluegrass hills and experience the magic of Kentucky's Bourbon Trail with an unforgettable stay at Daynabrook Farms. A full kitchen makes for effortless in-cabin dining, Private hot tub, scenic views of the countryside from your private back porch, convenient location to Lexington (20 min. to Airport), Louisville, Frankfort, and Danville. Areas around Hot tub, pools, and shower are wet, please exercise caution when in use.

The Robin's Nest

Welcome to the Robin's Nest, nestled in historical Harrodsburg, Kentucky! This recently remodeled 2-bedroom cottage is located in the heart of downtown, just steps away from boutiques, restaurants, bars and Old Town Park. Step inside The Robin's Nest and be greeted by a warm and inviting atmosphere. The living space is tastefully decorated creating a welcoming environment. Come celebrate the legacy of Harrodsburg the oldest city in Kentucky!

The Pleasant Hill Farmhouse

The Farmhouse has been designed for the travelers who want to get out of the city and soak up a quiet country sunset. This darling home is nestled on the edge of a 60 acre cattle farm and offers all standard amenities. It is favorably located to many attractions in Central KY: Shaker Village, Asbury University, EW Brown power plant, Centre College, Keeneland Horse Track, LEX airport, and within 25 miles of 8 distilleries on the Bourbon Trail.

Normans Cottage - Herrington Lake

Norman’s Cottage – Cozy Lakefront Getaway on Herrington Lake Escape to Norman’s Cottage, a charming 3-bedroom, 2-bath lakefront retreat designed for comfort, relaxation, and fun! Nestled on the peaceful shores of Herrington Lake, this cozy getaway offers everything you need for a memorable stay—whether you’re sipping morning coffee on the porch swing or soaking in the hot tub under the stars.