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The Towner

Conveniently located to some of the best spots Eastern Ky has to offer, and yet, The Towner still has the small town country charm that has come to be expected of the Red River Gorge area. Guaranteed clean and comfortable!! Perfect for extended stays or short “getaways”. Located within city limits, The Towner is perfect for those who like adventure with the convenience of the city. High Speed WiFi, within walking distance of groceries and Restaurants, yet only 8 miles to Slade Welcome Center.

Robbie’s Rest: Amazing Mountaintop Sunrises

2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible

The Retreat, 30 min from RRG/Natural Bridge

Modern 3 Bedroom 2 Bath on 11.5 acres roughly 20 miles from Red River Gorge. Entire house has been renovated. Starlink Internet, Electric fireplace, Smart TVs in all bedrooms/living room, Pinball Machine, and Ceiling fans in all bedrooms/living room. Fire-pit area with porch swing, chairs, bench for food, picnic table, and string lights for entertaining. The house sits on 11.5 acres, guests are welcome to walk the property. Large wrap around driveway for easy arrival/departure

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.

Cliffside Romantic Retreat LOVE

Fall in love at the unique and serene "Tis So Sweet Cliffside Cabin". The space is designed for a lovers retreat with luxuries of a spa bathroom, massage chair, fire table, recliner seat hot tub, and much more! This newly built cabin is peacefully secluded, yet still only a few miles away from the Natural Bridge State Park, Red River Gorge, Daniel Boone National Forest, underground kayaking, zip lines, rock climbing, swimming, delicious food and many other local attractions.

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.

Gateway to the Red River Gorge

Get off the beaten path at this unique and tranquil getaway. Situated atop a small hill on a ridge traversed by a dead-end road, the 510 sq ft cabin is on a wooded lot. Ideal for couples, it is a one bedroom with walk-out deck, large front porch, and a tv room with futon. It has a well-appointed kitchen area with new appliances, cherry and tongue and groove pine paneling throughout, vaulted ceiling, solid oak flooring, large picture windows, and a tv/work area.

Climbers Red River Gorge Getaway-Starlink

We'll have you feeling like a local in two days minimum and in a town so friendly you might just become one. One of a kind tiny home perfect for a weekend Red River Gorge getaway. Minutes drive from the best Red River Gorge hiking trails, climbing, Miguel's, Natural Bridge State Park, Hollerwood, Daniel Boone Backcountry Byway, The Gorge Underground, Callie's Lake, La Cabana & Kroger. Ample parking for multiple vehicles, or truck with trailer/sxs or crawlers.

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.

Red River Unit 4 - Feb. 20% Off Discount!

<b>20% OFF FOR A WEEK! 30% OFF FOR 28 DAY STAYS! STAY 30 DAYS OR MORE AND PAY NO TAXES! BEST VALUE FOR RED RIVER GORGE! CLIMBERS AND HIKERS WELCOME! 2 SEPERATE BEDROOMS </b> 12 miles to RRG, right next to Kroger. Easy access, no need for 4x4, its right in town! - Duplex right side - Central A/C and heat. - washer/dryer/gas stove - Fiber wifi - 4k Roku TV - Off street parking, private driveway fits 2 to 3 vehicles. PLEASE READ HOUSE RULES FOR PETS.

Maple Point - Dream Cabin in RRG

Welcome to Maple Point, an immaculate 1 bedroom + 1 bath cabin located in the heart of Red River Gorge. Completed in 2024, this property was thoughtfully created by a builder and designer to provide guests with a comfortable and memorable space to enjoy this region of Kentucky. Whether you are looking for a central base from which to explore, a quiet getaway where you can relax, or an inspiring space to work, we would love to have you come stay.