Holiday rentals in Boonesborough

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.

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

Harriet’s Hideaway: Amazing Mountaintop Sunrises

A rustic guest suite in the lower level of a log home. This open floor design features live edge tables, a large 75” screen tv with internet based channels, great wifi & an amazing view of the mountains & sunrises right outside your door! Your private deck has comfortable seating & a hot tub provided for your comfort. A Blackstone gas griddle is yours to use. A firepit with wood is provided! *Hosts do live upstairs, but the suite is sound insulated and noise from below has never been heard.

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

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.

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.

Prime Location! 2 Kings Patio Fenced Yard

Escape to our Guest Favorite boho-glam bungalow in Lexington's desirable Hartland area! This fully renovated 2-bed/1-bath home comfortably fits 4 with two king beds. Enjoy a stylish interior, a fully equipped kitchen, and a private, fenced backyard with a fire pit. Perfect for families, friends, and pets, you're just minutes from downtown, UK, and local distilleries. A chic and comfortable retreat awaits!