Holiday rentals with a fireplace in Woodford County

Timberframe on Farm Lexington, KY Solar Power

Our home and farm is very secluded and overlooks the KY River situated on the top of the Palisades. Minutes from Lexington, Keeneland, Shaker Village, Bluegrass Airport and the Bourbon Trail 5 bedrooms, vaulted ceilings, a 3000 SF home with screened porch and a hot tub. We have a good layout for wheelchairs and a portable wheelchair ramp if needed. Fire Pit, hot tub and hiking trails available. We use solar power for our energy needs! Our pond has no fish but we can direct u to a place to fish!

RIVER HOUSE at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Post & Beam home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites and horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant and Bourbon Bar. Scenic horse farms (ASHFORD, AIRDRIE, WINSTAR). Convenient to KEENELAND, KY HORSE PARK, Versailles, Midway, Frankfort, Lexington, Louisville! Hike, bike, fish, wildlife, sheep, goats, chickens, stars & firepit.

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.

Riverside Roost -bourbon themed water front home

Welcome to Riverside Roost! "The Roost" is nestled in a little community on the serene Kentucky River in Woodford County, although still close to Frankfort and Lexington. Yes, you are on the Bourbon Trail! While at The Roost, enjoy cooking on the grill, playing board games with the family, lounging on the deck or spending a day on the river. There are also plenty of distilleries and restaurants nearby. Whatever you do as the sun passes over and the river passes by, make memories together.

Home in Versailles on the Bourbon Trail

Guest house on beautiful 172-acre Country Estate in Versailles, KY (Woodford County). Large 4bd/3bth home located directly on Kentucky's famed Bourbon Trail and 15 minutes from the historic Keeneland Racetrack and Bluegrass (Lexington) airport. Bourbon fans will enjoy proximity to famous distilleries such as Woodford Reserve, Four Roses, Buffalo Trace, and more. Visit the locally famous Kentucky Castle and enjoy all the activities of the world renown Kentucky Horse Park and museum.

Midway Meadows Downtown on the Park

Best of Both! Very short walk to the eclectic downtown Midway and all its restaurants and specialty shops or walk out the back door and take your very own walking path to the Walter Bradley Park (see photos for Park and park map) which lead to several walking trails meandering along Lees Branch Creek. Relax on the large screened-in porch in the evening or make a fire in the great room. You will be pleasantly surprised when you step into this 1880’s restored railroad homestead.

*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

Greenwood Farm log cabin-pet friendly

It is a 200 year old log cabin in Woodford County on a cattle farm owned by the same family since the late 1700’s. It is located just 3.7 miles from the Kentucky Bourbon Trail, with 5 distilleries within 10 miles. It is a 20 minute drive to Keeneland Racetrack and the Bluegrass airport, 35 minutes to the Kentucky Horse Park and 1 hour to Churchill Downs. Another option is to spend time at the cabin enjoying the farm by either just sitting on the porch or walking.

The Cottage at Montresor

Certainly one of the most enchanting, smartest places to escape to. Everything about it is just right: stay at our splendid 50 acres just minutes from Keeneland. Relax in comfort surrounded by beautiful decor - all in proportion. An unrivaled ambiance of peace & tranquility with the convenience of contemporary living. This destination will leave you wishing you could stay forever. 5 minutes from restaurants & grocery, 12 minutes from the airport & luxury shops.

Relax in the hot tub with a view of the River!

Welcome to the Kentucky River Bourbon Cabin! Relax and rejuvenate in this cozy cabin nestled in a wooded setting & on the edge of the Kentucky River! Here you will find peace and serenity in nature with an upfront view of the water. Secluded and private yet still close to stores, restaurants and many tourist attractions such as major distilleries and wineries. Four Roses, Wild Turkey, Woodford Reserve and Buffalo Trace are just a short drive away.

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 .

Bourbon Trail Lakehouse - Pet Friendly!

Lake house? ✔️ 🛶 Bourbon Trail? ✔️ 🥃 Horse country? ✔️ 🐎 You’re sure to fall in 💗 with lake views, cozy bedding, modern decor & a well-stocked kitchen. Located in the capital on the Ky Bourbon Trail, this peaceful Lakehouse is sure to be the perfect getaway for couples, friends & families alike! Minutes to several distilleries, 10 mins to the Capitol, 30 mins to Lexington. Pets are allowed for $150 per stay.