Holiday houses in Stamping Ground

On The Rocks

Ultimate in privacy, yet two minutes from downtown Frankfort! This cabin-style home (think Gatlinburg!) sits on three wooded acres. Long, rambling decks on three sides (one covered, one fully screened, one open air). Our adjacent farm surrounds the property, making it even more private. This home sits high on a bluff above downtown Frankfort & the Kentucky River (our farm borders on the river). Just three miles to Buffalo Trace Distillery (if you could fly, it's way closer than that!)

Family · Value · Laundry

Private Farm Basement Apartment!

Basement apartment located on 5 acres in Central Kentucky! Full and private kitchen, dining& living; laundry available on main level of home if needed, 1BR with attached BA. Step outside your private entrance to the shared back yard and patio space. 6 minutes from the KY horse Park and 2 minutes from interstate 64. Pets welcome with non refundable deposit/ cleaning fee. Pet must be with you at all times or crated There are 3 dogs on property will only be in shared yard Trailer parking ok

Family · Location · Sleep quality

Griffith 1860 Log Cabin

Our 1860's log cabin is your perfect location. Close enough to tourist attractions and restaurants, yet away from traffic and distractions. Just 8 miles in the country from historic Georgetown, Kentucky, Kentucky Horse Park and Ark Encounter nearby. First floor bedroom has a queen bed with attached bath with tub and shower. Second floor bedroom with double bed, another second floor bedroom has 2 twin beds, sitting area day bed with trundle underneath. Bath with shower on second floor.

Value · Location · Access

Modern Farm Loft

Welcome to our serene newly constructed Modern Farm Loft. Upstairs, our two-bedroom retreat offers views of our goat farm and tranquil countryside. Enjoy relaxing after exploring Keeneland horse racing, the Bourbon Trail, the Ark Encounter, and The Kentucky Horse Park. Cook with farm fresh duck eggs in the fully equipped kitchen. Interact with friendly farm animals or even lease our horse stalls if needed. Unwind on the private deck or by the fire under the starry skies. Book your stay today!

Location · Family · Condition

Top Shelf the only Airbnb in KY above a Distillery

The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

Value · Family · Sleep quality

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

Location · Family · Air conditioning

Saxony Farm - The Dew Drop In

Nestled in the heart of Kentucky's Bluegrass region, The Dew Drop In, (newly constructed in 2018) is located on Saxony Farm, a working Thoroughbred horse farm, family-owned and operated for over 50 years. More than just a place to rest your head, guests will experience a home-away-from-home location, & enjoy the peace and quiet of farm life, all within striking distance of downtown Lexington, KY's Bourbon Trail, locally-owned restaurants, shops and numerous family-friendly activities.

Family · Location · View

New! Horse Farm stay! On Bourbon Trail!

The Loft at Pine Knoll Farm Kentucky is a unique horse farm stay located above our beautiful horse barn in the heart of horse country. We have prime views of the farm which is located in the center of the Bourbon Trail. 5 min to great restaurants in Midway! The Loft is 15 mins to The Kentucky Horse Park, 25 mins to Keenland, and Ark is 50 mins. Stabling/turnout available. We offer horse experiences/workshops/clinics through Kentucky Horse Experiences. Sign up to meet The Peace Ponies!

Value · Location · Condition

Quaint cottage on scenic horse farm

Welcome to the Cottages at Oxford Springs Farm. Enjoy a quiet stay in the largest cottage of our newly remodeled rental properties, all located on this beautiful, small working thoroughbred farm. Views from every window capture the beauty of the bluegrass. Conveniently located only 10 miles from the Ky Horse Park, 5 mi from the quaint historic town of Georgetown, and 30 minutes from some of Kentucky’s greatest bourbon distilleries. For wildcat fans, Rupp Arena is only 15 minutes away.

Family · Value · View

Spacious and quiet Grandma's Duplex

Roomy, out-of-town duplex, within 7 minutes of downtown Georgetown, KY. You will see farmland and livestock on your drive to your stay with us. We are 40 min from The Arc Experience; 15-25 minutes to Lexington attractions like the KY Horse Park, Keeneland, UK & Rupp Arena! Large rooms throughout. Queen bed in the master suite with a king bed in the guest bedroom, full eat-in kitchen and washer/dryer available. Great place for extended-stay, especially with the applicable discount!!

Location · Family · Parks

KY’s #1 Wishlisted Stay-Treehouse and outdoor tubs

Escape to Kentucky’s 2026 most wishlisted Airbnb! A romantic treetop getaway with two outdoor tubs, twinkle lights, and a peaceful setting made for reconnecting. The treehouse features a large glass rolling garage door allowing stunning views of the sunset. The highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station ✔ Hot Water

Value · Family · Parks

Downtown! Walkable | 6m Horse Park | Cozy Bungalow

Main St.'s "Hallmark Movie" charm awaits! Walk to dining, shopping, and sweet treats. Our five-star "guest favorite" bungalow is a clean, cozy, private retreat in Georgetown, KY. So many reasons for small families, friends & couples to stay: horse racing, tKentucky Horse Park (6mi), University of Kentucky, Georgetown College, 12-mile Legacy Bike and Scull Buster trails, near Bourbon Distilleries, ARK (30 min drive), cycling, and championship horse events. Easy driveway parking.

Value · Location · Parking