Holiday rentals in Boonesborough

Stylish Loft 2Bdrm Winchester ky near Lexington

New York style loft meets historic renovation—Central Kentucky. Meet charming Winchester. Under hr. to Keeneland race track, Kentucky Horse Park, & the spectacular Red River Gorge/Natural Bridge. Lexington 30 min. Paris, Georgetown, Richmond & Berea close too. Many local, small businesses-restaurants, brewery, distillery, shops, antiques, flea markets, & historical sites! Unit is on the second floor—may not be right for all abilities. Public, street parking. See our lovely town renovation.

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.

New! Mountain Top A-Frame Cabin, The Triangles

Escape to your mountain top sanctuary where breathtaking views leave you in awe . This newly constructed A-Frame cabin invites you to immerse yourself in the tranquility of nature while indulging in modern comforts. Relax in the hot tub while enjoying stunning sunsets and gorgeous nature views all around. With meticulous attention to detail, each corner of this retreat exudes a personal touch, ensuring a truly unforgettable getaway amidst the wilderness. 20 mins to RRG! The Triangles

Modern Townhome Close to UK

Welcome to this modern townhome, located in the desirable Chinoe neighborhood. Steps away from Chinoe Shopping Center, you'll find a supermarket, salon, and several restaurants. It's just a quick drive to Kroger Field, and a short drive to the heart of downtown. So whether you're here to place a bet at the Keeneland racetrack, attend a concert at Rupp Arena, tour one of our many bourbon distilleries, or cheer on the Wildcats, you'll find that this townhome is in a convenient location.

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

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.

Our Cottage is a perfect retreat for adults only

Boone Creek Cottage is a private home for adults only located on a scenic byway in the heart of the Bluegrass Region. We are close to Boone Creek, Raven Run Nature Sanctuary, 2 restaurants on the Kentucky River, and 3 wineries yet only 15 minutes from downtown Lexington. We are conveniently located about 3.3 miles from I-75 with easy access to the Bourbon Trail, the Kentucky Horse Park, and other Central Kentucky attractions. IG account: boonecreekcottage

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)

Stunning Cedar Cabin, Hot Tub, Amazing Views!

Escape to this serene cabin surrounded by 20 acres of green hills. This cedar cabin is only 15 minutes from Richmond KY, but you'll feel like you're in a different world. Admire the nature through floor to ceiling windows, roast marshmallows on the patio with a chimenea, and melt your stress away in the Artesian Premier hot tub. Experience a peaceful stay in this quiet and comfortable retreat.

Premium A-Frame • Hot Tub • Sauna • Pond & Animals

Private 58-acre A-Frame retreat in the Kentucky Appalachians with mountain views, a stocked fishing pond, hot tub, infrared sauna, fire pit, games, and rare farm animals. Meet Suffolk Punch draft horses, a Highland cow and calf, and Thoroughbreds by request. No TV by design, just nature, stillness, connection, and a true farm-stay experience. Sleeps 7.