Holiday rentals in Boonesborough

Luxury on Main / East

Head past the custom front-door painting and into an interior with original hardwood flooring. Standouts include a remote-control fireplace and subway-tiled kitchen with stainless steel appliances. A wood stove adds a warm glow to the shared patio. This 1920's shotgun-style four unit apartment building has been completely restored with all modern amenities. The Tenant House has a rich history on Main Street in downtown Richmond. Guests have access to all shared spaces I will be available 24/7 for contact via text, call, email, or in person. Information about the surrounding area and the unit will be provided. Walk to the latest downtown venues and jog round nearby parks from this location, directly across from the Richmond Visitors Center. Eastern Kentucky University is also convenient for here, while many places to eat and drink are on the doorstep.

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.

Romper Ridge

Enjoy one of the best veiws in the Red River Gorge from our beautiful cliffside cabin! • Loft style bedroom with a king-size bed, and a private bedroom with a queen-size bed on the first floor. • Starlink internet/wifi • Well appointed kitchen • Shower with a veiw in our newly installed outdoor shower. (Seasonal) • The cabin is located 20 minutes from the Slade exit off the Bert T Combs Mountain Parkway. • Right at the center of all the hiking, climbing, and exploring the Gorge has to offer!

The Lodge at Marble Creek

Escape to The Lodge at Marble Creek, a modern cabin tucked in the woods overlooking beautiful Marble Creek and its palisades. This 3-bedroom, 2-bath getaway sleeps 6 guests. Relax in the hot tub, unwind in the sauna, or enjoy a soak in the spa-style tub. Gather by the indoor or outdoor gas fireplaces, or end the night around the firepit under the stars. Just minutes from Nicholasville and Lexington, yet it feels like you’re deep in the Gorge — peaceful, private, and surrounded by nature.

Westwood

Stay in this newly renovated, freshly furnished 3 spacious bedroom 3.5 bathroom home in the heart of Richmond, KY. This home has many luxury features like a sunroom, granite countertops, and is walking distance to Eastern Kentucky University’s Campus. Included is a Smart TV in the living room, TVs in 2/3 bedrooms, adjustable AC/Heat, Serta Mattresses, and luxury furniture perfect for relaxing. We appreciate you staying with us, and feel free to reach out at any time during your stay!

KY’s #1 Wishlisted Stay-Treehouse and outdoor tubs

Escape to Kentucky’s 2026 most wishlisted Airbnb! A romantic treetop getaway with two outdoor tubs, twinkle lights, and a peaceful setting made for reconnecting. The treehouse features a large glass rolling garage door allowing stunning views of the sunset. The highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station ✔ Hot Water

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.

Riverview 2 … enjoy the view !

Enjoy the spectacular views of the Kentucky River from this second-floor studio. Located within an easy walk of hiking trails and dining. Visit the Waterfront Grill or Hall’s on the River. A tasting at the winery just a few minutes away will sweeten your stay. For more play, kayak rental is nearby. This property is nestled on the riverbank. You will encounter bugs if you are enjoying the outdoors. We have regular exterminations, but an occasional cob web is to be expected.

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.

Relaxing Hot Tub | S’mores Fire Pit | Garage

Stay in one of Lexington's most desirable neighborhoods: quiet, safe, & in a low-traffic cul-de-sac that's also close to everything! Create lasting memories with friends & family: - Make s’mores by the fire pit under the stars! - Relax in the hot tub after a long day of travel! - Fenced in yard! - Coffee Bar! Just minutes from favorite local restaurants, shopping, attractions, downtown events, & the interstate (I-75 or I-64). Registration #15076499dash1

Unique Stay - 1907 Log Cabin Near Kentucky River

Kirkland Cabin - Stay in a 1907 Log Cabin Perched on the Palisades of The Kentucky River in Lexington. * 2022 Updated Kitchen * King Bedroom and fun loft offering 2 single beds (ladder access) & 1 full bath. This is a cabin built in 1907 & has the character to prove it. Unplug with games or utilize High-speed WiFi. This cabin is 1 mile from I-75 & 15 minutes to downtown Lexington. Enjoy dinner < 1 mile away at Proud Marys BBQ w/ Live music (seasonal)

Newly Built Town & Country

Newly built, cozy home in the heart of Richmond. Walking distance to downtown Richmond and directly across from a brand new city park. Conveniently located to EKU & I-75. Spacious, open feel with 3 bedrooms (king bed in primary on the mainfloor, 2 queen beds upstairs ) and 2.5 baths. Amenities include granite countertops, stainless appliances, washer & dryer, smart TV's in each bedroom, tile showers, & WiFi.