Lloguers vacacionals a Winchester

Luxury on Main / East

Head past the custom front-door painting and into an interior with original hardwood flooring. Standouts include a remote-control fireplace and subway-tiled kitchen with stainless steel appliances. A wood stove adds a warm glow to the shared patio. This 1920's shotgun-style four unit apartment building has been completely restored with all modern amenities. The Tenant House has a rich history on Main Street in downtown Richmond. Guests have access to all shared spaces I will be available 24/7 for contact via text, call, email, or in person. Information about the surrounding area and the unit will be provided. Walk to the latest downtown venues and jog round nearby parks from this location, directly across from the Richmond Visitors Center. Eastern Kentucky University is also convenient for here, while many places to eat and drink are on the doorstep.

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.

The Flower Pot

Welcome to The Flower Pot! Come and stay at our newly renovated mid century modern home complete with a record player collection and great natural sunlight. This location is a hidden gem in Lexington! HIGHLIGHTS: - One turn off main road for easy access to ALL attractions and necessities in Lexington - The Distillery District, Rupp Arena, Keeneland, Red Mile(Railbird Music Festival), UK Campus all approximately 10 MINUTES OR LESS - 1 King bed/ Two Queen Beds with smart TVs - New luxury bathroom

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 Discount April 30 /May 1,2 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

Richmond Retreat by Raydarr Properties, LLC

Older home with lots of character located within walking distance of downtown Richmond. If you like the outdoors there is a porch with a swing, and a sitting area in the back yard with a fish pond. Located approx. 2 miles off of I-75. The driveway goes behind the house for parking, and is quite narrow. There is plenty of room in the driveway to park out front (which is also safe), if you are unable to squeeze through. The driveway side of the yard is open, so the backyard is not fully fenced.

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.

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.

Luxury A-Frame Retreat | Hot Tub, Sauna & Fishing

Escape to an A-Frame retreat in KY, where valley views and thoughtful comforts invite you to slow down and create meaningful memories. ✓ Soak in the hot tub under the stars ✓ Relax in the infrared sauna + private gym ✓ Gather around the fire pit, pool table, and ping pong ✓ Enjoy the stocked fishing pond + pedal boat ✓ Great for couples, families, and small groups Sleeps 7 comfortably, space for 8 upon approval. No TV by design—for slowing down, reconnecting, and enjoying nature.

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.