Pet-friendly 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.

Bluegrass Country Cottage

Enjoy a quaint, private, quiet & charming little place to call your own, on a small, working (seasonal) Thoroughbred horse farm. Green acreage, lovely scenes and sunsets. Located in horse country, between historic Winstar Farm and Lane's End Farm, just a short drive to small town USA, Versailles; historic Midway; and to the nearby City of Lexington, home of the Kentucky Wildcats, Horse Capital of the World, Bourbon Country & so much more. Pets allowed (2 max), well behaved, pet fee applies.

Bourbon Barrel Cottages #2 on the Kentucky Bourbon Trail

Leave the Cleaning to Us – Your Bourbon Country Escape Awaits! Kick back, relax, and unwind in a stylish, serene retreat nestled in the heart of Kentucky’s Bourbon Country. Welcome to Bourbon Barrel Cottages, where nature, comfort, and convenience come together. Each of our five private two-bedroom cottages sits on its own two-acre lot, surrounded by wildlife and natural beauty—perfect for couples, friends traveling together, or anyone seeking peace and privacy. You'll Love Staying with Us!

Creekside- Bourbon Trail Oasis

Welcome to Creekside, a unique vacation experience nestled in the heart of Versailles, KY. Steeped in nature, Creekside offers majestic views of the river with peaceful waterfalls. In the evening, gather round the crackling fire pit, creating memories under the stars. When you're ready to explore, you'll find downtown Versailles is just a 10-minute drive away. For bourbon lovers, we are just 25 minutes from the famous Woodford Reserve. We now have Starlink wifi to always keep you connected!

Hillside Farm & Creek - A Bourbon Trail Retreat

Reconnect with nature at this unforgettable escape. Hillside Farm is a peaceful paradise located in the heart of horse and bourbon country. It is a serene and natural setting tucked away but only 8 miles from downtown Versailles. You will stay in a tobacco barn converted into a charming cabin making for a unique and memorable experience. Sit on the large, covered porch and enjoy the sweeping views of the hillside overlooking Clear Creek. It is a nature, horse, and bourbon lovers dream!

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.

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.

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 .