Places to stay near Wildside Winery

Chic Cabin w/ Trails, Hot Tub & Starry Nights

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

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.

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Distillery District Diamond-pet friendly

This 1948 bungalow in an up-and-coming neighborhood has two bedrooms/one bath. This house has all the updates you could ask of modern living including internet access, TVs with Roku, and keyless entry. Each bedroom has blackout curtains, ceiling fan and bedside power station. The bath is fully stocked with essential personal care items. The fenced-in back yard has a deck and a fire pit. STR Reg #15075605-1. Maximum occupants 4-Guests are prohibited from allowing more than maximum occupancy

Lexington Apt. with parking & private entrance

Lower level apartment with parking and two entrances. Light painted walls, ceiling lighting/fan, plus free washer and dryer. Approximately 10-15 minutes from Bluegrass Airport, 15-20 minutes to the University of Kentucky campus, stadium and 20-25 to Rupp Arena, 10-15 minutes from main entrance to Keeneland Race Track Main entrance, 20-25 minutes to downtown Lexington, 10-15 minutes to shopping mall/restaurants located in mall area, 50 minutes from the ARK ENCOUNTER AND CREATION MUSEUM.

Mountain Dream Cabin -Fish Pond+Fenced Yard+Stalls

Escape to a peaceful cabin with a wraparound porch perfect for soaking in the beauty of nature. This pet-friendly retreat features a fenced yard and space for trailer parking, plus four horse stalls available upon request. Enjoy catch-and-release fishing in the stocked pond, or explore nearby attractions: 25 minutes to Berea’s historic downtown and Pinnacle Trails, and 30 minutes to Flat Lick Falls and Sheltowee Trace. Unwind, explore, and experience the charm of our small-town getaway!

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

Cottage Circle Home

This charming home is nestled in a cozy neighborhood, offering a serene atmosphere and a strong sense of community. Conveniently located, it boasts easy access to a variety of restaurants, catering to different tastes and cuisines, just a short stroll away. Keeneland Racetrack, a track that runs in the fall and spring months, is only 8 minutes from the driveway! Additionally, a nearby grocery store ensures that daily essentials are within reach. Cottage Circle is waiting for YOU! ☺️

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

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!!

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.