Family-friendly vacation rentals in Woodford County

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Top-rated family-friendly rentals in Woodford County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

An airy living space is showcased, featuring large windows that invite natural light and provide views of the surrounding fields. Comfortable seating arrangements with a mix of couches and chairs are positioned around a central area rug, highlighting a handcrafted coffee table and a wood stove.

Chalet in Wilmore

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!

FamilyIndoor spacesSleep quality

4.92 out of 5 average rating, 158 reviews

Top guest favorite

A paved driveway stretches into the distance, flanked by lush green grass and a large tree. Wooden fencing borders the property, offering views of rolling hills and a colorful sunset sky above.

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.

KitchenIndoor spacesOutdoor spaces

4.99 out of 5 average rating, 171 reviews

Top guest favorite

The home is nestled amidst a backdrop of gently rolling hills, framed by trees showcasing autumn foliage. A welcoming front porch is visible, accompanied by a small staircase leading to the entrance. Large windows allow natural light to filter into the living space.

Home in Versailles

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.

Indoor spacesKitchenLocation

5.0 out of 5 average rating, 152 reviews

Top guest favorite

A cozy living area is presented with a television mounted on the wall. A black leather sofa faces a small wooden coffee table and two armchairs. Natural light filters through the windows, complemented by patterned curtains, creating a warm atmosphere.

Cottage in Salvisa

Cottage on the Bourbon Trail

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 June-Sept. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

Indoor spacesKitchenParks

4.97 out of 5 average rating, 157 reviews

Top guest favorite

A charming two-story home features white siding and dark shutters, framed by lush greenery and seasonal decorations. A welcoming path of brick leads to the entrance, where decorative pumpkins add a touch of warmth, inviting guests to explore the property.

Home in Midway

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!

FamilyKitchenWalkability

4.99 out of 5 average rating, 108 reviews

Top guest favorite

The exterior of The Dew Drop In is framed by two large trees, showcasing a well-manicured lawn. The house, painted in light colors, is set back from the foreground, with a wraparound porch visible. A wooden fence outlines the property, enhancing the natural setting.

Farm stay in Midway

Saxony Farm - The Dew Drop In

Nestled in the heart of Kentucky's Bluegrass region, The Dew Drop In, (newly constructed in 2018) is located on Saxony Farm, a working Thoroughbred horse farm, family-owned and operated for over 50 years. More than just a place to rest your head, guests will experience a home-away-from-home location, & enjoy the peace and quiet of farm life, all within striking distance of downtown Lexington, KY's Bourbon Trail, locally-owned restaurants, shops and numerous family-friendly activities.

FamilyKitchenAccess

5.0 out of 5 average rating, 133 reviews

Top guest favorite

A spacious lounge area is visible, featuring a leather sofa and a vintage chest serving as a coffee table. The open kitchen is equipped with modern appliances, while warm lighting from a nearby lamp adds a cozy ambiance to the space. Light-colored walls complement the wood flooring.

Guest suite in Wilmore

Kinlaw Valley-View Hideaway

Your "hideaway" is conveniently situated in the Bluegrass and Bourbon Trail region of beautiful central Kentucky, just a few miles south-west of the eclectic city of Lexington. You are a short walk from Asbury University/Seminary and from the Centennial Park. Keeneland Race Track, The Kentucky Horse Park, UK, and Bluegrass Airport are within a short half hour's distance. The Daniel Boon National Forest, the Ark Encounter and Churchill Downs are each within a 90-minute picturesque drive.

KitchenFamilyNearby

4.98 out of 5 average rating, 102 reviews

Top guest favorite

A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.

Home in Versailles

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

Indoor spacesKitchenBreakfast

4.95 out of 5 average rating, 249 reviews

Guest favorite

Home in Versailles

Woodford Stables / Walk to Eckert's Orchard

Welcome to Woodford Stables, your serene retreat nestled amidst rolling hills and picturesque paddocks. This charming farmhouse boasts a modern kitchen, three inviting bedrooms, and two pristine bathrooms. Relax in the cozy living area, or step outside to savor breathtaking views. With horses grazing nearby, it's a tranquil escape. Conveniently located, you can stroll to Eckerts Orchard for a delightful local experience. Ask us about boarding your horses during your stay!!

Indoor spacesKitchenDecor

4.84 out of 5 average rating, 149 reviews

Top guest favorite

A spacious bedroom is featured with a large, dark bed framed by two bedside lamps. A soft, blue throw blanket adorns the bed. A painting is displayed on the wall above, and a potted plant adds a touch of greenery in the corner.

Home in Wilmore

*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

Indoor spacesKitchenDecor

5.0 out of 5 average rating, 109 reviews

Top guest favorite

Cabin in Lawrenceburg

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.

FamilyKitchenBathroom

4.99 out of 5 average rating, 302 reviews

Guest favorite

A functional kitchen features modern appliances, including a stove, refrigerator, and coffee maker. Light streams through two windows, illuminating the wooden countertop and the unique round window above the sink. A rustic wooden bar with seating creates a welcoming breakfast area.

Cabin in Versailles

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 .

KitchenFamilyBreakfast

4.96 out of 5 average rating, 158 reviews