Holiday rentals in Woodford County

4.97 out of 5 average rating, 136 reviews

Cottage in Salvisa

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!

4.98 out of 5 average rating, 320 reviews

Flat in Wilmore

Basement apt. w/private entrance & kitchenette

Our full basement apartment with private entrance is modest but comfortable. Located within one mile of Asbury Seminary and University, our space is ideally suited for commuting students, out-of-town guests, or folks visiting the beautiful Bluegrass region. Our home is a 15-minute walk from the campuses and business district. We are a family of six and you will occasionally hear our boys upstairs, but as a Christian family, we strive to treat our guests as we would want to be treated. Reg. 9485

5 out of 5 average rating, 31 reviews

Tiny home in Versailles

Bluegrass & Bourbon Cozy Cottage

Welcome to our cozy cottage in Woodford County, right on the Kentucky Bourbon Trail! Just a 10-minute walk to downtown, you'll find coffee shops, restaurants, bakeries, parks, & The Amsden Bourbon Bar. Iconic spots like Woodford Reserve, Castle & Key, & Keeneland are all within 7 miles. Though visible, the quiet cottage is tucked away with a private drive, offering a peaceful retreat. Whether you're into bourbon, horses, hiking, or just relaxing, you’ll feel right at home. Book any tours early!

4.99 out of 5 average rating, 119 reviews

Farm stay in Frankfort

The Cottage at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Restored log home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites & horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant & 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 & campfires.

4.98 out of 5 average rating, 337 reviews

Flat in Versailles

High style on the Bourbon Trail

Historic 1 bedroom apt in the heart of horse country & the bourbon trail. Quiet bedroom. Central Main St. location in charming Versailles, steps from local coffee shop & bourbon bar. Walk to food, shopping and park. Light filled apartment with vaulted ceiling and exposed brick wall. Cozy bedroom has memory foam Cal king bed and percale cotton sheets. The decor is an eclectic mix of antiques, Ferrick Mason textiles, wallpapers and Alex K Mason original art. Parking space. Free washer & dryer.

4.9 out of 5 average rating, 111 reviews

Home in Kentucky

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.

4.99 out of 5 average rating, 128 reviews

Home in Midway

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!

5 out of 5 average rating, 57 reviews

Flat in Versailles

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.

4.91 out of 5 average rating, 445 reviews

Farm stay in Versailles

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.

4.95 out of 5 average rating, 187 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

4.92 out of 5 average rating, 301 reviews

Cabin in Nicholasville

National Historic O'neal Cabin

Originally built during the late 1700’s, this two-story log cabin was restored in 1995. The O'neal Cabin is listed on the National Register of Historic Places. Located in central Kentucky, six miles from historic downtown Lexington, the O’Neal Log Cabin is in the heart of horse country and the bourbon trail. Whether you are looking for a getaway, a place to stay during the horse sales or a retreat while you visit Lexington’s sites, the O'Neal Log Cabin is perfect retreat.

4.93 out of 5 average rating, 291 reviews

Flat in Wilmore

Travelers Loft - Asbury & Lexington area apartment

You deserve a unique and simple guest experience! Your full apartment in Wilmore has an upstairs sleeping loft. ► A short walk to Asbury University and Seminary ► 25 minutes to Lexington, Keeneland, and UK ► A quiet neighborhood with green space ► Upstairs loft bedroom with low, pitched ceilings ► Secure keyless entry ► Hi Speed Internet ► Roku TV ► Peaceful & secure ► Keurig coffee maker ► One set of towels and sheets for stays less than a week

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Popular amenities for Woodford County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Woodford County

5 out of 5 average rating, 36 reviews

Home in Midway

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

EthanRating, 5 stars4 days ago

The Mint Tulip was awesome! The driveway did sneak up on us the first time, but it was super easy to turn around and once we knew where we were heading, we never missed it again. The basement mini golf was a super cool activity, as well as an impressive pickleball court. Overall, we had an amazing time with a beautiful place to stay!

4.76 out of 5 average rating, 67 reviews

Flat in Frankfort

Charming Apartment on the Bourbon Trail

DebbieRating, 5 stars3 weeks ago

Beautiful spotlessly clean home with a comfortable king size bed, full kitchen with washer and dryer and lovely living room to relax and read or enjoy tv.

5 out of 5 average rating, 4 reviews

Bourbon Trail & Keeneland Charm

LaurieRating, 5 stars1 month ago

This place was great! Our host replied within minutes every time. I asked her a question. We felt at home. She had great suggestions and was very friendly. Will definitely use them again!

4.74 out of 5 average rating, 39 reviews

Flat in Versailles

Spacious Apartment With Hidden Room

Marjorie LeaRating, 5 stars1 month ago

What a beautiful Kentucky countryside home away from home! Everything was lovely and spit spot; thank you for sharing your home suite, so that we could spend time with our family in the area.

Guest house in Versailles

4.83 out of 5 average rating, 6 reviews

Garden cottage

RonaldRating, 5 stars2 weeks ago

We just loved staying at Loretta‘s Garden cottage. It felt like the Secret Garden when we first walked onto the property! We loved the kitty cats wandering about, purring, and making friends with us. Everything about the cottage was comfortable, peaceful, squeaky clean and full of charm! We felt right at home. We would not hesitate to stay here again.

4.68 out of 5 average rating, 71 reviews

Home in Lexington

Silver Streak Retreat

DebbieRating, 5 stars2 weeks ago

I was pleasantly surprised... Not only was the home nicer than I expected but the accommodations were outstanding and the Host/Co-host were top notch! I personally did not meet Deb in person but she was quick and friendly to respond to my messages. I did get the privilege of meeting co-host Julia who was SUPER nice, friendly, helpful, and overall a great person. We were very comfortable and felt welcomed. Definitely would recommend to anyone considering going to Lexington to stay here. I know if I go back I know I will be staying here again! Absolutely made our whole experience even better!!!

5 out of 5 average rating, 39 reviews

The Lily Pad - 2 Bedroom Bluegrass Bungalow

LindaRating, 5 stars1 month ago

This is our second time staying at the Lily Pad. We stayed five nights, our longest, and were quite comfortable.. The location is great for the things that we like to do in and around Versailes. It’s much better than a hotel room, with a nice living room, full kitchen and laundry. I wish there was some outside seating for morning coffee, but we just took it to the Life Adventure Center farm and enjoyed my daughter’s beautiful gardens. 🌸