Holiday houses 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.

Fireflies & Fables, our cozy Red River Gorge cabin

It’s time to plan your 2026 getaway to the gorge! Located on 2 acres, escape with your family or friends to our secluded, pet friendly Red River Gorge cabin where you’ll sleep on a brand new mattress and wake up every morning to the relaxing sounds of nature. You can start your day with coffee or a book on the peaceful screened in porch, take an afternoon hike, 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!

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!

Charming Historic apartment

Welcome to your perfect getaway in the heart of historic downtown Mt. Sterling! This beautifully restored upstairs apartment combines vintage charm with modern comforts, offering a unique and cozy retreat just steps away from local shops and restaurants. Step inside and enjoy the character of warm hardwood floors, and bright skylights that fill the hallway with natural light. Whether you’re here for a weekend or a longer stay, you’ll love the charm and comfort of this unique downtown gem.

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.

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!

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.

Welcome to the Bunkhouse!

The bunkhouse boasts 3 large bedrooms, two offer queen beds, while the master has a king. Two full baths and an additional sectional couch in the living room guarantee you plenty of room to spread out and enjoy your stay! Enjoy a peaceful stay on a working rare breed horse farm surrounded by large herds of both young and old horses as well as other farm animals. Gorgeous sunsets are as common as the gorgeous equines spotting the 70 acre farm.

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.

Five O’clock Somewhere

A brand new studio home w luxury king bed, tile shower In full bathroom, and kitchen! Located in downtown Mt. Sterling! WiFi Smart TV Coffee maker Fridge Microwave Hot plate 5 minute walk to downtown Mount Sterling ! 4 minutes from I-64 exit Bring your pet and stay with us! This is a brand new home, yard still needs seed and straw and 14 steps to get into home out front! On street parking