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LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the KY Horse Park and downtown Lexington. 30min to Keeneland. 45min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, fooseball and butlers pantry w/ coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.

Spring Street Loft by Rupp-Covered Parking + Deck

Brand new 2nd-level loft with free covered parking spot beneath, a huge deck and outdoor dining option. Directly across Maxwell St. from Rupp Arena's parking lot-you can't get any closer! This single unit building was built on stilts to maximize outdoor space and downtown views. Your perfect oasis in the middle of the action includes a full kitchen, laundry room, bathroom, living area and Smart TV. Come for a concert or stay awhile, you'll have everything you need during your trip to Lexington!

KY & Bourbon & Horses, Oh My! Close to Keeneland

This home has been completely renovated with flawless finishes and top of the line appliances. This is for the UPSTAIRS only. (No one else lives at the residence & is solely for Airbnb) 10 minutes from Keeneland & a few miles from hospitals. Convenient location to shopping and restaurants. Clean and comfortable living spaces. This is a chefs kitchen, that has double doors to a walk out patio. The bathroom has a Bluetooth fan. I’ve provided everything to make your trip enjoyable as possible.

Robbie’s Rest: Amazing Mountaintop Sunrises

2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible

Guest Fav + Quiet & Romantic + Hot Tub + Fire Pit

Lil Red cabin is about 30-45 minutes from Red River Gorge, Natural Bridge, Underground Kayak and Cave Run Lake. Whether hiking, a wedding, romantic weekend or just getting away, Lil Red is the place! The cabin has been a favorite for visitors to the area for many years. Some of the favorite features are the year-round hot tub, large back deck, charming living room with gas fireplace to sit and read a book, play board games or watch the Smart TV. Come stay and relax in Lil' Red.

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older non-gentrified neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

Cliffside Romantic Retreat LOVE

Fall in love at the unique and serene "Tis So Sweet Cliffside Cabin". The space is designed for a lovers retreat with luxuries of a spa bathroom, massage chair, fire table, recliner seat hot tub, and much more! This newly built cabin is peacefully secluded, yet still only a few miles away from the Natural Bridge State Park, Red River Gorge, Daniel Boone National Forest, underground kayaking, zip lines, rock climbing, swimming, delicious food and many other local attractions.

Carriage House Gardenside

Privacy and Convenience are yours when you stay at the Carriage House Gardenside. Located in historic Winchester, Carriage House Gardenside offers easy access to Lexington, the Kentucky Horse Park, Keeneland Race Course, the Bourbon Trail and Red River Gorge. Situated across from College Park and steps away from Winchester's public gym (indoor swimming pool and fitness center). Space features a king sized bed, large TV, coffee bar, devoted work space and full bath.

Suspended SkyView Cabin Near RRG

Welcome to Skyview Cabin! A unique all wood construction suspended over a cliffside. What sets our cabin apart is its unique perch – suspended 30 feet up in the air, offering a truly elevated experience. The property is peacefully secluded, yet just a short 20 minute drive to Red River Gorge. Enjoy a nice soak in the hot tub after taking part in all the RRG has to offer : swimming, kayaking, boating, biking, fishing, golfing, hiking, caving, and rock climbing.

Climbers Red River Gorge Getaway-Starlink

We'll have you feeling like a local in two days minimum and in a town so friendly you might just become one. One of a kind tiny home perfect for a weekend Red River Gorge getaway. Minutes drive from the best Red River Gorge hiking trails, climbing, Miguel's, Natural Bridge State Park, Hollerwood, Daniel Boone Backcountry Byway, The Gorge Underground, Callie's Lake, La Cabana & Kroger. Ample parking for multiple vehicles, or truck with trailer/sxs or crawlers.

The Winchester Retreat

Welcome to the Winchester Retreat! We are located right off of I-64 in Winchester, just 30 minutes from both Lexington and the Red River Gorge. We're right down the street from Winchester's downtown, boasting restaurants, breweries, and shops. Pet friendly!! Come spend an evening by the fire pit and whip up a great dinner using our fully equipped kitchen or charcoal grill. We're also close to Legacy Grove Park, complete with a walking trail and dog park.

Maple Point - Dream Cabin in RRG

Welcome to Maple Point, an immaculate 1 bedroom + 1 bath cabin located in the heart of Red River Gorge. Completed in 2024, this property was thoughtfully created by a builder and designer to provide guests with a comfortable and memorable space to enjoy this region of Kentucky. Whether you are looking for a central base from which to explore, a quiet getaway where you can relax, or an inspiring space to work, we would love to have you come stay.