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Vacation rentals in North Middletown

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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

Other great vacation rentals in North Middletown

Cabin in Slade
Fireside, Extraordinary Couples Cabin
$127 per night
Dome in Wolfe County
"Home Sweet Dome" MODERN TREEHOUSE STAY w/ Hot Tub
$236 per night
Cabin in Frenchburg
Modern Cabin Nestled on 40 Acres w/ Hot Tub
$133 per night
Cabin in Stanton
Seclusion Cabin - Tower, Treehouse, Koi Pond
$259 per night
Tiny home in Powell County
NEW! Hot Tub! Tiny Hūs Retreat in the Woods
$115 per night
Cabin in Stanton
Elderberry Cabin w/ Hot Tub near Red River Gorge
$146 per night
Cabin in Slade
Hidden Little Gem @ RRG - - Tanzanite!
$193 per night
Private room in Paris
Paradise Inn B&B - Lover's Suite
$105 per night
Home in Mount Sterling
THE DOLLY - Cozy, Bright Home in Historic Downtown
$65 per night
Cabin in Powell County
Lets Get CozyRRG, hot tub, wifi, no clean/pet fee!
$161 per night
Home in Paris
The Spring Valley Inn - charming rural home
$137 per night
Loft in Mount Sterling
One Bedroom apartment with full kitchen
$79 per night