Places to stay in Winchester

Magnolia Molly | Rupp Arena, Distillery District

Welcome to Magnolia Molly - a peaceful and centrally located home. Our 2-bedroom property sleeps 4-6 guests and has ample entertaining and relaxation space. Walk to all the Distillery District has to offer: delicious restaurants, coffee, craft beer, and the Burl music venue. Located 5 minutes from downtown Lexington, Rupp Arena, and Red Mile. Drive just 10 minutes to Kroger Field, Keeneland, & the airport; 20 minutes to KY Horse Park. 2 security cameras on premises at points of entry.

Climb On Inn- RRG-3 BR & 2 BA- Outdoor Paradise

CLIMB ON INN- Experience serene living in this 3-bedroom, 2-bath home nestled in the heart of Red River Gorge. Ideal for outdoor enthusiasts, this property features a spacious primary bedroom with an en-suite, new rustic game room, and a large front porch perfect for enjoying nature. Beautifully decorated interiors along with an experienced host ensuring a clean and comfortable stay. Pets welcome, making it a delightful retreat for families or groups seeking adventure climbing the Red!!

Kentucky Horse Farm Barndo On The Bourbon Trail

My place is close to Shaker Village, Old Fort Harrod State Park, Historic Beaumont Inn, Bright Leaf Golf Course, Pioneer Playhouse, Perryville Battlefield State Historic Site, Danville KY, Centre College. You’ll love my place because of the views, the location, the horses, the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Also close to Four Roses Distillery, Wild Turkey Distillery, Wilderness Trail & Buffalo Trace & Makers Mark

The George- Beautifully Furnished, Walk Downtown

Located in downtown Georgetown, this lovely historic home has been freshly updated and is centrally located to all of the area attractions! This property offers a fully stocked kitchen, work space, a great back yard, and laundry. We also provide Matrix hair products, Buff City soaps, and Starbucks coffee (we like to spoil our guests)! Short walk to the great shops and restaurants downtown and Georgetown College. Care-free checkout- no chores! We can't wait to have you here!

The Bourbon House- Downtown Lex’s Premier Air B&B

Welcome to "The Bourbon House" Downtown Lexington's Premier spot to stay for an authentic Kentucky experience. This cottage was built by me from the ground up with no details spared to immerse my guests in the finest things Kentucky has to offer- Fully stocked bourbon bar mixers! (You supply bourbon) Hand crafted house and furnishing from reclaimed wood and bourbon barrels, private hot tub, bathrobes, garden, fire pit, and walking distance to downtown and Rupp arena

Traveler's Cottage

Beautiful Craftsman style Bungalow in the heart of Berea. This two bedroom, two bath cottage has off street parking and is a short walk to Artisan Village/Old Town, galleries, shoppes, and cafes. Step into a beautiful, comfortable, clean environment featuring original art, hardwood floors, tall ceilings, queen sized beds. Basic TV channels, Roku, and High Speed Internet. Walk to Nightjar dinner, Native Bagel for breakfast or an early lunch. Great neighborhood!

Paradise Inn B&B - Lover's Suite

The only B&B in Kentucky with an ‘Eiffel Tower’ view! Paradise Inn B&B is a unique penthouse suite atop "The World's Tallest Three Story Building" (from Ripley's Believe It or Not!) with exquisite oriental decor from the far East. The unbeatable hospitality is provided by your host and the owner, Lee Nguyen. This stay includes a $25 gift certificate for Paradise Cafe - Asian fusion and Pho restaurant located on the first floor.

Berea Bungalow

Indulge in a remarkable stay at our quaint bungalow in Berea, KY! We are conveniently located off I75, and only a stone's throw away from Berea College & Old Town. Treat yourself to some authentic local cuisine, discover the city's thriving artisan culture, or embark on an exhilarating hike in the nearby breathtaking "Pinnacles". Boasting 4 plush beds and 2 baths, this home can comfortably accommodate up to 6 guests.

RRG/Jacuzzi/Fire pit/ WiFi/ New Cabin/Nature trail

Welcome to Peaceful Pines Cabin where you are sure to find a peaceful, beautiful, and private place to relax in the RRG, less than 10 minutes to restaurants and scenic trails. Gorgeous sunrises and sunsets can be seen here. This cabin was built by a family to enjoy the beauty of the RRG.