House vacation rentals in Woodford County

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Top-rated house rentals in Woodford County

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Guest favorite

Home in Lawrenceburg

4.98 out of 5 average rating, 61 reviews

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**

Guest favorite

Home in Versailles

5 out of 5 average rating, 62 reviews

Birdsong Valley on Bourbon Trail

Great central location on Bourbon Trail. Close to Lexington, airport, Keeneland, Ride the Rails, Horse Park, Shakertown, many other attractions. You will love our 3 bedroom charming home on 2.2 beautiful acres in peaceful community. Perfect for couples, friends, families, singles to explore distilleries, horse farms, quaint small towns of Versailles, Midway, Lawrenceburg, country backroads, much more. OR relax, enjoy nature, butterflies, birds, deer. Let us make lodging highlight of your visit.

Guest favorite

Home in Midway

5 out of 5 average rating, 64 reviews

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.

Guest favorite

Home in Midway

4.99 out of 5 average rating, 116 reviews

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!

Guest favorite

Home in Midway

4.99 out of 5 average rating, 80 reviews

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!

Guest favorite

Home in Frankfort

4.92 out of 5 average rating, 63 reviews

The Bourbon Sanctuary

Recently remodeled home on the Bourbon Trail! This home has 2 bedrooms & 2 baths with a king size bed in one room and a queen in the other. Close proximity to several distilleries and local wineries here in the bluegrass state! You will find a peaceful atmosphere along with some horse farms on your drive to the distilleries. This home is within a mile of Castle & Key distillery and Woodford Reserve! The sunsets are beautiful and you will most likely see wildlife right outside the back door!

Guest favorite

Home in Versailles

5 out of 5 average rating, 12 reviews

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.

Guest favorite

Home in Harrodsburg

4.93 out of 5 average rating, 238 reviews

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

Guest favorite

Home in Versailles

4.95 out of 5 average rating, 158 reviews

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

Guest favorite

Home in Wilmore

5 out of 5 average rating, 52 reviews

*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

Guest favorite

Home in Frankfort

5 out of 5 average rating, 150 reviews

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.

Guest favorite

Home in Versailles

5 out of 5 average rating, 19 reviews

Ancient Oaks - Spacious Home - 6 mi to Keeneland

Charming 1800s brick home with about 1,800 sq ft of living space. Privacy fence with gate surrounds about 1/2 an acre of the side and back yard. Local brewery, coffee shops, restaurants, shopping, grocery store and even a Farmer's Market, when in season, all within a mile. Located on the Bourbon Trail. Just 6 miles from Keeneland/BG Airport, 13 miles from Rupp/downtown Lexington, 20 miles from KY Horse Park.