House holiday rentals in Woodford County

The Stagg House on the Ky River

Nestled on the Kentucky River in Frankfort, KY, our peaceful retreat is surrounded by historic chestnut trees and wildlife like deer & cardinals. Just 5 miles from Buffalo Trace, 6.7 miles from Castle & Key, and 10 miles from Woodford Reserve and Whiskey Thief, it’s ideal for bourbon enthusiasts. Enjoy the river beach, backyard BBQs in summer, or cozy nights by the fireplace in winter—wood provided. Fully stocked kitchen, pet and family-friendly, with a secluded vibe yet close to the main road.

Country Cottage in Horse and Bourbon Country

This completely updated cottage is located on a scenic byway voted one of the ten best scenic drives in the United States, on which you will see thoroughbred farms for which Kentucky is famous. Keeneland and the Kentucky Horse Park are within 20 minutes. There are 4 distilleries within 10 miles, 11 within 30 miles, and 23 within an hour’s drive. Two bedrooms, new kitchen, new bathroom, washer and dryer, covered porch, deck, air conditioning, wifi, cable TV, and ample parking. Relax and enjoy!

Willow Springs 2br/1ba- Sleeps 8 33 acres w/trails

Built in 2023, this barndominium sits at the end of a private drive surrounded by woods and horse farms. 2 bedrooms (queen and full w/twin trundle), a queen pull-out sofa and full futon comfortably sleep 8. Located only 4 miles from Bluegrass Parkway, there is quick access to local dining, the Bourbon Trail and Rail Explorers. Amenities include Wi-Fi, a laundry room, full kitchen / dining area, patio with grill, and a nature trail through the forest. The reviews tell it better than I do!

Whiskey Woods: Newly Remodeled w/ HOT TUB!

Discover Whiskey Woods in picturesque Frankfort, KY! This 3-bed, 2-bath retreat on 3.6 acres offers modern amenities. Enjoy open-concept living, a fully equipped kitchen, and outdoor dining. Explore the lush property with grill. Sleep in plush beds, including a king-sized Whiskey Suite. Stay connected with Wi-Fi, laundry, and parking. Only 1.4 miles from Castle and Key Distillery, and 4.9 miles from Woodford Reserve. Minutes from downtown attractions. Book your Frankfort getaway today!

Kentucky Horse Farm Barndo On The Bourbon Trail

My place is close to Shaker Village, Old Fort Harrod State Park, Historic Beaumont Inn, Bright Leaf Golf Course, Pioneer Playhouse, Perryville Battlefield State Historic Site, Danville KY, Centre College. You’ll love my place because of the views, the location, the horses, the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Also close to Four Roses Distillery, Wild Turkey Distillery, Wilderness Trail & Buffalo Trace & Makers Mark

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

Woodford Stables / Walk to Eckert's Orchard

Welcome to Woodford Stables, your serene retreat nestled amidst rolling hills and picturesque paddocks. This charming farmhouse boasts a modern kitchen, three inviting bedrooms, and two pristine bathrooms. Relax in the cozy living area, or step outside to savor breathtaking views. With horses grazing nearby, it's a tranquil escape. Conveniently located, you can stroll to Eckerts Orchard for a delightful local experience. Ask us about boarding your horses during your stay!!

*KY Charm*Asbury-Lex-Keeneland-King bed-spacious

This spacious, private basement is the perfect lodging for visiting families, commuting students, or out-of-town explorers. Located in a peaceful subdivision in the quaint town of Wilmore, we're within walking distance to Asbury University and Seminary, Centennial Park, hiking trails, and a bustling main street with shops, cafes, and restaurants. We are an easy 20-30 minute drive from Lexington, Keeneland, Rupp Arena, and the Bluegrass Airport. Jess Co Permit #9248

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

Step into the stylish and bright 3BR 1BA one-acre oasis in the heart of the picturesque bourbon country. It promises a relaxing retreat just a few minutes from local distilleries, scenic countryside landmarks, and exciting attractions. ✔ 3 Comfortable Bedrooms ✔ Bright Living Area ✔ Full Kitchen ✔ 9-hole Duck Duct Putt-Putt Golf Course ✔ DIY Pickleball Court ✔ Vintage Jukebox ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking See more below!