Vacation rentals in Montgomery County

Historic 2-Bedroom Apartment in Downtown

Charming apartment in the historic Farmers National Bank building in downtown Mount Sterling. Recently renovated, the apartment provides the comfort and amenities of home, yet retains all of the character of the original building. Within walking distance of many great restaurants and if you’re in the mood to shop, stop in to Lily Aesthetics downstairs or take a stroll down Main Street to find a variety of great shopping opportunities. Located within 35 miles of Lexington and the Red River Gorge.

Endless View Cabin Rental

Endless View Cabin is conveniently located in the Red River Gorge/Natural Bridge area. It is a new construction (970 sq. feet of open floor plan). Bedroom 1 includes 1 queen size bed, dresser, hi-chest, nightstand and 55"TV. Bedroom 2 boosts a huge 4 adult queen size, Minnesota pine bunk bed with dresser. This cabin is dog friendly, loaded with board games for the family, has an outdoor fire pit, amazing views, quiet and secluded which allows for a great getaway for you and your friends/family.

Barndo|Hot Tub|Sauna|Fire Pit|20 min RRG|Rec Room

Luxury Barndominium | Ultimate Game Room | 20 Mins to Red River Gorge This newly designed luxury Barndominium is packed with every amenity and game you can dream of, making it perfect for families, groups, and adventure seekers exploring the Red River Gorge, stargazing by the fire pit, lounging, or soaking in the hot tub. Games for all ages include pool, foosball, ping pong, darts, arcade games, multiplayer video game table, small child play area, pickleball, basketball, volleyball, and more!

Rustic Mt. Sterling Cabin1 Near Downtown • Pets OK

Rustic Mt. Sterling Cabin 1 Near Downtown • Pets OK ★☆ ABOUT THIS SPACE ☆★ Tucked away in the rolling hills of Mt. Sterling, this rustic cabin offers the perfect blend of country charm and modern comfort. Just a short drive from the historic downtown district, you’ll have easy access to local shops, dining, and small-town charm—then come home to peace and quiet. Inside, unwind with a movie on the 55" smart TV, play a round of cards, or cook up something hearty in the fully equipped kitchen.

Firethorn’s Hilltop Haven

Country living at its finest. The home is nestled on a 140 acre seasonal working farm with lush open fields in scenic rural but Central Kentucky. This peaceful getaway gives a glimpse of what life on the farm and being in nature is like. Surrounded by open rolling fields, the perfect place to relax, take a walk, take a dip in the pool, or just be in nature. This home has it all. Family friendly. Pool available from May 19th to September 9th. Rates apply. Can park RV's & trailers.

Fireflies & Fables, our cozy Red River Gorge cabin

Located on 2 acres, escape with your family or friends to our secluded, pet friendly Red River Gorge cabin where you’ll wake up every morning to the sounds of nature. You can start your day with coffee or a book on the peaceful screened in porch. Take a walk up the hill for views of the valley. Find an afternoon hike to see the natural arches in the area, and wind down with a board game or s’mores by the fire. Whatever your adventure, we hope you'll make lasting memories in our cabin!

THE DOLLY - Cozy, Bright Home in Historic Downtown

Hello, Dolly! This bright and cozy home in the heart of downtown Mt. Sterling provides comfort and convenience. With hundreds of unique artifacts and rare photos to discover, you will find peace, relaxation, and tons of Dolly-themed photo ops! In addition to WiFi and Roku TV, guests will enjoy a massive collection of Dolly Parton films, records, and books. A fully-themed kitchen, bedroom, dining room, and bathroom offer many fun Dolly touches. A place so cute, even Jolene wants to stay!

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!

Pawplex

✨ Modern Pet-Friendly Retreat – Right Next Door to the Dog Park! ✨ This stylish, fully renovated 1-bedroom studio is designed for comfort, accessibility, and furry friends. You’ll love falling asleep to the soft hum of downtown while knowing your pup has their own cozy crate and the best dog park in town just outside the door. Come experience downtown living that’s stylish, accessible, and truly dog-approved! We can’t wait to host you and your four-legged best friend! 🐾

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.

Cozy Woodland Cabin -20 Min to Red River Gorge

Tucked away in the rolling Bluegrass hills, Elk Track Trail Cabin is a peaceful escape into nature — just a scenic 20–25 minute drive to world-class hiking at Red River Gorge and Natural Bridge State Resort Park. Follow a picturesque country drive to a private retreat, where you’ll feel immersed in the woods while still enjoying the comforts of home. It’s the perfect balance of cabin comfort and that nostalgic “camping under the stars” feeling.

Magnolia bluff

Forget your worries in this spacious and serene space. Enjoy a multi-functional therapeutic massage in the heated massage chair while watching the 55 inch smart tv. The zero gravity massage chair provides a full body relaxation from the neck down to the legs. Get a great workout without leaving the privacy of your home. Dedicated work out room with an elliptial machine, rowing machine, weights, push-up bars, yoga mat and more.