Holiday houses in Harrodsburg

The charming exterior of the house features a white facade with dark shutters. A welcoming front porch is accessed by concrete steps, which are flanked by neatly trimmed shrubs. An American flag proudly waves at the side, adding a touch of local character.

4.91 out of 5 average rating, 150 reviews

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!

4.87 out of 5 average rating, 267 reviews

The exterior of a charming red barn is shown, featuring white accents and a welcoming front door. A wreath adorns the door, and colorful autumn decorations are placed at the base, complemented by lush greenery and a peaceful sunset backdrop.

Barn in Harrodsburg

The Beaumont Parlor, 8 miles to Shaker Village

It's rare to find a place that's both historic & one-of-a-kind. That's exactly what you are going to get at The Beaumont Parlor! Formerly an old milk barn & milk parlor for the City of Harrodsburg, this newly restored unit features old world charm & all the modern amenities a guest could ask for. Featuring a King bed, Queen Sleeper Sofa & Full Bathroom. The Owner's have spared no expense and you will find charm at every angle. Guests will be able to walk to Beaumont Inn & Downtown Harrodsburg

4.95 out of 5 average rating, 243 reviews

An expansive deck presents scenic views of Herrington Lake, bordered by trees for a natural ambiance. Outdoor seating with a table invites relaxation, while the gentle waters below contribute to a peaceful setting.

Cottage in Harrodsburg

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!

4.94 out of 5 average rating, 207 reviews

The Betsy Sweat Cottage.

View the cottage on YouTube listed by the name of the cottage. Previous Guests have described the interior as (Quirky) …..compliment…August2026 UPDATES —- New flooring in bathroom and kitchen..New queen mattress and arrangement of furniture..This home is all Electric . Carbon Monoxide detector located beside bed .This is a Small Home. Close to Danville 9.5 miles (15 minutes away). , Frankfort 32 miles (40 minutes away). *** Notice. Neighborhood Highlights has Hosts Guidebook info .***

4.96 out of 5 average rating, 202 reviews

An outdoor area is visible, featuring a fire pit surrounded by several chairs and a picnic table. Lush green grass is present, complemented by trees in the background. An active railroad bridge looms above, with soft, diffuse light filtering through the clouds.

Cabin in Wilmore

Highbridge River Cabin, Private Dock, EV Charger

Relax at the river cabin. Retreat right on the Kentucky River with private dock for easy river access. The cabin has Dual Plug Type 2 EV charger. Cozy cabin on stilts with stone fireplace & porch with table and chairs. Surrounded by nature & beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 mins or less from LEX Airport, Keeneland and Shaker Village. No extra guests without permission, no parties.

A modern, two-story home is set against a backdrop of trees, showcasing a combination of dark siding and warm lights from the windows. A wooden staircase leads to an inviting entrance, while a gravel path provides access to the property.

4.97 out of 5 average rating, 58 reviews

Normans Camp - Herrington Lake

Escape to this beautiful 3-bedroom, 3-bathroom home on the serene shores of Herrington Lake in Harrodsburg, KY. Whether you're seeking a peaceful getaway or an adventure-filled vacation, this lakeside retreat offers the perfect blend of comfort, recreation, and natural beauty. With its stunning lake views, prime location, and ample amenities, this Herrington Lake house is your ideal escape for a memorable vacation. Book your stay today and start making memories at this lakeside gem!

Superhost

4.89 out of 5 average rating, 198 reviews

Private Getaway on Bourbon Trail w Hot Tub

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.

4.97 out of 5 average rating, 107 reviews

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!

4.96 out of 5 average rating, 164 reviews

Two horses are depicted, one dark brown and the other light chestnut, standing side by side. They are adorned with riding gear, their eyes focused on the landscape ahead, which features rolling hills blanketed in greenery and autumn foliage.

Farm stay in Harrodsburg

The Bunkhouse at Big Red Stables

There is no better way to experience Kentucky than horseback riding the rolling hills of the Bluegrass. Big Red Stables is happy to offer the Bunkhouse to visitors who want to ride horses, travel to nearby bourbon distilleries, go to the races or events at the Kentucky Horse Park, or just get away from it all on a third generation family farm. Horseback riding by appointment only as arranged with your hosts.

4.93 out of 5 average rating, 74 reviews

The Luxe/Hot Tub/Putt Putt/10 Miles Shaker Village

Discover the Perfect Setting! Nestled on the renowned Bright Leaf Golf Course within the historic town of Harrodsburg, Kentucky, this delightful duplex offers a private two-bedroom, two-bathroom apartment on its left side. Be captivated by nearby attractions such as Shakertown, Old Fort Harrod State Park, the KY Bourbon Trail, Centre College, and a plethora of other exciting destinations

Superhost

4.79 out of 5 average rating, 105 reviews

Lakefront - Breathtaking Views - Bourbon

Lakefront villa on Herrington Lake Sleeps 12 • 3BR + bunks Private dock + boat slip Fish, swim, or relax right off the water Amazing fishing Underwater fish light illuminates lake at night Kayaks & paddleboards included Spacious lake house with room for families & groups Chef’s kitchen Fast, reliable Wi-Fi Game room (pool table, shuffleboard, arcade) Minutes to the Bourbon Trail

4.98 out of 5 average rating, 127 reviews

Home in Nicholasville

Cuttawa House

Find your home away from home at Cuttawa House, a luxurious three bedroom home, perfectly appointed. Featuring woodwork harvested directly from the property, dramatic gas fireplace, and an outdoor living room, the Cuttawa House offers both the solitude and peace of the bordering woods as well as beautiful views of rolling horse fields.

Popular amenities for Harrodsburg holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Harrodsburg

4.98 out of 5 average rating, 55 reviews

A modern one-story home is showcased, featuring a dark exterior with contrasting wooden porch posts. Blue outdoor chairs are arranged invitingly on the covered porch. A spacious driveway leads to an oversized garage, with a lawn area visible in the background.

Home in Burgin

New Quiet Retreat Hot Tub Shaker Village Danville

Superhost

4.5 out of 5 average rating, 8 reviews

Stay at the Fort Street Inn

An outdoor deck area features comfortable seating, a hot tub, and a charcoal grill among lush greenery. The living room showcases a cozy gas fireplace with horse-themed decor and ample natural light. A dining area with a large table is also visible, enhancing the inviting space.

4.96 out of 5 average rating, 67 reviews

Hot Tub | 3 King Suites | Bourbon Trail

A wooden walkway is visible beside a landscaped area, leading towards a sign that reads 'Lake House.' An air conditioning unit and a storage container are present along the pathway, with glimpses of the lake seen in the background.

5.0 out of 5 average rating, 25 reviews

Graceful Relaxation on the Lake

4.96 out of 5 average rating, 79 reviews

An open living area features a vibrant area rug with swirling colors, complemented by a navy blue sectional and a light wood floor. A flat-screen television is mounted on the wall, while natural light fills the space through large windows, illuminating cozy seating areas.

Cottage in Harrodsburg

Cozy Tree House @ Herrington Lake near Lexington

4.97 out of 5 average rating, 36 reviews

A beautiful view of a sunset casts warm hues across the sky, illuminating a tranquil outdoor space. A fenced pool area is surrounded by lush greenery and colorful flowers, with a pathway leading to a charming barn and farmland beyond.

Apartment in Harrodsburg

The Nook at Castaway Farm

The entrance features a pair of elegantly crafted wooden doors with intricate glass designs, set against a stone facade. Flanking the doors are potted flowers and rustic elements, such as a barrel and a vintage container, enhancing the welcoming ambiance.

4.93 out of 5 average rating, 42 reviews

Braxton Manor at Creekside Retreat

Two lounge chairs are positioned on a spacious deck, overlooking a scenic view of Herrington Lake. An umbrella provides shade, while a potted plant adds a touch of greenery. The tranquil waters and tree-lined shoreline are visible in the background.