Vacation rentals in Winchester

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the KY Horse Park and downtown Lexington. 30min to Keeneland. 45min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, fooseball and butlers pantry w/ coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.

Right Angle Country*Remote*Hot Tub~NO Cleaning FEE

Behold peaceful country living, a secluded homestead, where modern comfort meets rustic charm. Tucked away on a narrow country road, this remote sanctuary offers true escape. Wander our private trail, curl up with a book by the fireplace, immerse & reinvigorate in the hot tub, pause in hammock, gather around a crackling fire under a blanket of stars. Wonderfully secluded, just 15 min from town, located between the adventures of RRG & Lex, offering the perfect blend of isolation & accessibility.

Life is Better On The River

Make lasting memories at this unique and family-friendly cottage on the Kentucky River. Enjoy nature at its best, along with all the comforts of home. With a pool, hot tub, and putting green there is plenty to do to unwind. Guests return year after year. This property is located on the riverbank. You may encounter bugs while enjoying the outdoors. We conduct regular exterminations to reduce encounters. You will also enjoy the songs of many birds, glow of lightening bugs, and seeing the stars.

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.

Family Farm Winchester/Lexington 20 min.*Game Room

Franklin Ridge Farm 5 minutes to DT Winchester Lexington 20min. Easy access 5min. I64; 15min. I75 / I64 Discounts Weekdays in July Centrally located: Eateries & Historical Sites Lexington 20min State Parks Meadow Green Music Park 20min Keeneland 30.4mi. Kentucky Horse Park 30min Red River Gorge 35min Ark Encounter 45min Creation Museum 1hr 30min ~Home is surrounded by our family farm beginning of Scenic Rt.15 *All guests must be registered to see price of your stay before booking

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.

The Carriage Inn - 1-bdrm apt in historic downtown

Centrally located in historic downtown Winchester with views of the county courthouse. Apartment is upstairs in a building that was originally used as a carriage repair shop. It is within walking distance to lots of unique shops and restaurants and the Bluegrass Heritage Museum. Walk or drive to the Farmers Market (seasonal) on historic Depot Street on Saturday mornings. The Red River Gorge/Natural Bridge area is 40 minutes east. Lexington is a short 20-30 minutes west.

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.

1800’s Historical Log Cabin Lexington KY

Welcome to your authentic 1820s log cabin near Boone's Station in Lexington, Kentucky! As you step inside, you'll find yourself transported back in time to the early 19th century, but with all the modern conveniences you could need. The cabin has been lovingly restored and modernized, so you can enjoy the charm of pioneer living without sacrificing comfort. Hi-Speed wifi onsite. within 1 mile to I-75

Stunning Cedar Cabin, Hot Tub, Amazing Views!

Escape to this serene cabin surrounded by 20 acres of green hills. This cedar cabin is only 15 minutes from Richmond KY, but you'll feel like you're in a different world. Admire the nature through floor to ceiling windows, roast marshmallows on the patio with a chimenea, and melt your stress away in the Artesian Premier hot tub. Experience a peaceful stay in this quiet and comfortable retreat.

Bourbon on the Hill

Brand new studio home just built! King size bed w a Purple brand luxury mattress, tile shower in full bathroom, WiFi, kitchen and much more! Everything u need for a relaxing stay! Includes washer and dryer! 4 minutes from 1-64 1 minute from downtown Mt Sterling Come and enjoy! 14 steps to climb to get to front door The yard work still needs seed and straw but it’s ready for ur visit !