Vacation rentals in North Middletown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in North Middletown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private room in Paris

Farm Stay With Amazing Views

Nestled in the lush bluegrass farm country of Bourbon County Kentucky, Hidden Hollow Farm offers a great, quiet get away. Enjoy watching the thoroughbred mares graze. You might be lucky to see the yearlings frolic a bit, too. The farm is 20 acres of bluegrass and mature trees. We are limiting our stay to this beautiful room overlooking the back pasture. It has it's own Private Entrance and bath. Paris, Mount Sterling, Fort Boonesborough, and more are nearby.

$60 per night

Barn in Paris

Horse & Flower Farm Barn Apartment

Enjoy peace and quiet in the countryside surrounded by Stoner Creek. Old Bridge Farm is the home to two businesses. One is a horse farm and the second is 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 apartment above with all of the conveniences of home, including wifi and Roku TV. Come...relax, escape, recharge.

$126 per night

Home in Winchester

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Double bed, kitchen, living room, dining all in one place. *update! we've upgraded to a queen size bed! 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.

$60 per night

SUPERHOST