House holiday rentals in Woodford County

Bourbon Barrel Cottages #4 on Ky. Bourbon Trail

LEAVE THE CLEANING TO US! Kick back and relax in this calm, stylish cottage 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. We’re located directly between 4 of the biggest bourbon distilleries on the trail and 20 min from anything! Sit out on your deck or at your own private fire pit at night and listen to the sounds of birds, frogs and other wildlife. **There will be a $500 for smoking inside of the cottage**

Midway Cottage-Vineyard, Bourbon Trail, Horses

Enjoy the great outdoors at Saddlestone Cottage, an old family farm house fully renovated offering all new amenities. It's in heart of horse country, but close to everything...Ky Bourbon Trail, Ky Horse Park, Keeneland, Equus Run Vineyards, Old Friends, and historic Midway. Excellent dining choices are close by in Midway, Lexington, Georgetown and Frankfort. You have the perfect front porch view of picturesque Equus Run Vineyards, located just across the road, and access to South Elkhorn Creek.

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.

Bourbon Central! Prime Location and Amenities

Welcome to your ideal mid-term home in Kentucky. Located 3 minutes from downtown Versailles, this spacious 4-bedroom, 2.5-bath residence is perfect for traveling professionals and corporate stays. Situated in Bourbon Country, it's a short drive to Lexington, Frankfort, Georgetown, and Lawrenceburg. Close to major employers, hospitals, and distilleries, this home offers both convenience and comfort. Relax in expansive living spaces and enjoy all the comforts of home during your extended stay.

The Bees Wing

Built in 1889 this 2800 sq ft home has lots of charm and plenty of space to accommodate up to 8 guests. With two king beds, a queen, two twins, a pull out sofa bed, plus three full baths, dining room, living room, completely remodeled kitchen, plus a spacious screened in porch overlooking the 16 x 40 in ground salt water pool and fabulous backyard, what more could you ask for in the heart of horse country? The heart of Midway with its renowned restaurants and galleries is just a block away!

Bourbon Trail Beauty

Enjoy this 2023 Fully Restored Gus Macey Victorian in downtown Versailles. Only one block walk to historical Versailles and conveniently located on the Bourbon Trail. 15 mins from Keeneland Racetrack; 20 mins from downtown Lexington. Comfortable for groups of up to 8 with easy access to Woodford Reserve, Castle&Key and Buffalo Trace distilleries. Or tour the world famous Horse Farms, including Coolmore Farm, only minutes away. Have your own Old Kentucky Home in the heart of Kentucky.

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

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.