Holiday 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.

Cottage w/Jacuzzi - centrally located, comfy beds!

Keep it simple at this peaceful & centrally-located house with hot, clean jacuzzi year-round (jets are old!). Comfy beds, cozy linens & a good sleep are the hallmark of our BnB. The focus is family, friends & interacting through good ol’ conversation. Plenty of room in kitchen for good meals! Lots of books in the library for a good read & art from local artists - all for sale. Close to downtown, campus, NOLI District, New Circle, I-75/I-64. Great stay for traveling professionals, nurses/doctors.

Serene Country Refuge at The Right Angle * Remote

Find your breath here. Behold peaceful country living, a secluded homestead retreat 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 from our library by the fireplace, or gather around a crackling fire under a blanket of stars. Though wonderfully secluded, just 15 min from town, located between the adventures of RRG & Lex, offering the perfect blend of isolation & accessibility.

Family Farm Winchester/Lexington 20 min.*Game Room

Franklin Ridge Farm is 5 minutes to DT Winchester close to Lexington 20min. Easy access 5min. I64; 15min. I75 / I 64 *Sale-Feb /March 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 EST 1803 beginning of Scenic Rt.15 *All guests must be registered to see price of your stay before booking

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.

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.

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. Guests return year after year. * WiFi is sometimes unreliable. It connects via satellite, as this is the only option available in our neighborhood. WIFI Riverstar, Pw 12345678 This property is located on the riverbank. You may encounter bugs while enjoying the outdoors. We conduct regular exterminations, but occasional cobwebs happen.

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

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.

Historic Cabin - Farm - Near RRG, Lex, local music

Join Laura, the founder of Laura's Lean Beef, Laura's Mercantile and Regeneration Distilling Co., at her farm at the edge of the bluegrass. The entire 1200 acres are open to guests, with easy access to the Red River Gorge, Winchester and Lexington. See farm animals and organic crops such as hemp, check out the aging barn for whiskey, while staying in an 18th century cabin updated with granite countertops, new beds and mattresses, modern bathrooms, and solar panels.

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.