Vacation rentals in North Middletown

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

The Tisbury House

Welcome to the Tisbury House - a charming 3 bedroom farmhouse nestled in the heart of Kentucky horse country! Located on a working horse farm in Paris, this serene getaway offers a unique blend of rustic charm and modern comfort. Whether you are here to explore the beautiful Bluegrass region, attend equestrian events or simply unwind, our home is the perfect base for your stay. We are located 25 mins from downtown Lexington, the Kentucky Horse Park, & Fasig Tipton and 40 mins from Keeneland.

Misfit Farm

Need to get away? Misfit Farm sits 700’ from the road, offers 3 bedrooms, a spacious kitchen & dining area for family meals and a theatre room to enjoy. 2 bedrooms have queen beds and 1 has a twin daybed with a trundle underneath. After a long day you can enjoy the 10' x70' covered porch while watching the sunset. 6 guests can make this a home base for visiting local farms, horse events and bourbon trails. We are just 40 minutes from Lexington where you can enjoy Rupp Arena & Keeneland.

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

High Street Hideaway home atmosphere for relaxing

High Street Hideaway, relax away from the city in a spacious well appointed home atmosphere. Large back deck for relaxing and dining. No need to park on the street and walk a flight of stairs! Private parking with 4-5 steps up to deck and back door! *Access to Lexington 30-45 minutes away via Interstate 64. * 45 minute drive to the natural beauty of Red River Gorge for hiking/ climbing *30 min to Cave Run Lake * Three blocks to local shops, eateries, and town festivals!

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.

Horse & Flower Farm Barn Loft

Enjoy peace and quiet in the countryside surrounded by Stoner Creek. Old Bridge Farm is a horse farm and also the home of Blooms of Bourbon County which is a flower, fruit and vegetable grower utilizing organic growing practices. Our 100 year old tobacco barn has been converted into a stable with a large rustic loft above with all of the conveniences of home. We're off the beaten path on a very quiet road in the middle of horse country. Come...relax, escape, recharge.

The Winchester Retreat

Welcome to the Winchester Retreat! We are located right off of I-64 in Winchester, just 30 minutes from both Lexington and the Red River Gorge. We're right down the street from Winchester's downtown, boasting restaurants, breweries, and shops. Pet friendly!! Come spend an evening by the fire pit and whip up a great dinner using our fully equipped kitchen or charcoal grill. We're also close to Legacy Grove Park, complete with a walking trail and dog park.

Paradise Inn B&B - Honeymoon 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.