Vacation rentals with outdoor seating in Woodford County

Cottage on the Bourbon Trail

Newly built cottage located in the country. Enjoy amazing views from a covered front porch as you rock in comfortable rocking chairs. Fully furnished and beautifully decorated to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a kitchen for cooking if desired. Pool is behind owners residence and is shared with owners family and possibly 2 additional people. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

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.

Top Shelf on the Bourbon Trail

Discover the perfect blend of history, charm, and excitement at The Top Shelf in downtown Versailles. Our beautiful two-bedroom apartment on Main Street puts you steps away from restaurants, a bourbon bar, coffee shop and park. Centrally located with Keeneland Racetrack and Kentucky's most celebrated distilleries like Woodford Reserve, Buffalo Trace, and Castle & Key, just minutes away. The Top Shelf is the ultimate destination for those seeking comfort, style, and adventure in Versailles, Ky.

Bourbon Barrel Cottages #2 on the Kentucky Bourbon Trail

LEAVE THE CLEANING TO US! Kick back and relax in this calm, stylish space in the center of Kentucky’s Bourbon Country. Enjoy wildlife and nature in one of our 5 two bedroom cottages. Each sits on two acres. Perfect retreat for couples traveling together or individuals looking for privacy and quiet. We’re located directly between 4 of the biggest bourbon distilleries on the trail and 20 minutes from anything you’d like to see and do! **There will be a $500 for smoking inside of the cottage

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.

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

Handcrafted Rustic Cabin on the Bourbon Trail

The cabin has been entirely built by the owner, Doris, (with help from family and friends) from reclaimed and local salvaged materials. Located on a beautiful Kentucky Scenic byway, on a working farm, the cabin is only 15 minutes from Wild Turkey Distillery, the town of Versailles , golf courses, dining, shopping, wineries and other major distilleries. 35 minutes from Keeneland race course, downtown Lexington, UK, Rupp Arena, the Horse Park and more .

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Limestone Landing is a modern, fully renovated, open space home in a country neighborhood setting. The home is the perfect retreat for your next getaway to Kentucky. Conveniently situated only a 1/4 mile from Castle and Key Distillery and 2 miles from Woodford Reserve. 1/2 mile from the highly rated restaurant and bourbon bar, The Stave. Indulge in the ultimate bourbon tasting experience, knowing that comfort awaits you at your cozy haven.

Charming Historic Home in Downtown Versailles

Experience early American architecture while enjoying modern conveniences in the Carter House. This unique, newly renovated first-floor apartment is located in the Versailles historic district, in easy walking distance of restaurants and shops. It’s the perfect place for a family or a group of friends to relax, enjoy time together, and visit surrounding sites. The host lives in the apartment upstairs and can be available if any issues arise.