Vacation rentals in Mount Sterling

Premium A-Frame Retreat | Hot Tub, Sauna & Pond

Escape to a peaceful A-Frame retreat in Irvine, KY, where valley views, thoughtful comforts, and private outdoor spaces invite you to slow down and reconnect. ✓ Hot tub under the stars ✓ Infrared sauna + private gym ✓ Fire pit, pool table, and ping pong ✓ Private pond, pedal boat + catch-and-release fishing ✓ Day trips to Nada Tunnel, Red River Gorge & Berea Pinnacles ✓ Great for couples, families & small groups Sleeps 7; space for 8 upon approval. No TV by design—to slow down and reconnect.

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 May 26,27 / June 20, 27 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.

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.

Seclusion Cabin - Tower, Treehouse, Koi Pond

Seclusion is a completely custom, hand-crafted cabin complete with a treehouse room, koi pond, rocky landscape, observatory tower and more in an unbeatable location. This cabin is located just a mile or two off the Slade, KY exit on top of a ridge in Red River Gorge. Built by Paul Rhodes in his spare time, this passion project took over six years to complete and boasts a uniqueness unrivaled by other accommodations.

Briar Patch Cabin-RRG | Fire Pit | Sunset | Wi-Fi

Located along the outskirts of the Red River Gorge Scenic Byway, The Briar Patch is perfectly situated to host travelers who are seeking both privacy and convenience. This cabin was thoughtfully designed to host anywhere from 1 to 6 people without making guests feel too cramped or in a space that’s too large to feel comfortable. Its rustic interior creates the perfect mood for this dreamy mountaintop vacation home.

Scenic views, farm fun in peaceful modern cottage

A family-friendly farm that offers opportunities for couples, families or small groups to create special memories. Our farm is also the perfect place for unique family adventures, family reunions, retreats, parties of any type and intimate weddings - all in an idyllic country setting (events charged separately). We offer educational tours and introductions to our animals for guests that are interested.

Hilltop Retreat at Wendt’s Wildlife Adventure

Take it easy at this unique and tranquil getaway. Newly remodeled home on a 125 acre farm that is home to Kentucky’s newest wildlife park & Daniel Boone’s last home in Kentucky. Expansive views, and a visit to Wendt’s Wildlife Adventure (open seasonally), which is owned & operated by your hosts, are sure to give you just the right amount of rest & adventure that you are seeking.