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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.

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.

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

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.

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)

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!