Holiday houses in Montgomery County

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.

Modern Barndo|Hot Tub|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, a dedicated small child play area, basketball, volleyball, and more!

Rustic Mt. Sterling Cabin2 Near Downtown • Pets OK

Rustic Mt. Sterling Cabin 2 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.

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.

Barn at Red River Gorge & Lexington

Location! Location! Location! Located only 15 minutes from Red River Gorge and Natural Bridge and 45 minutes from Lexington, this BRAND NEW 2 bedroom 1 bath barn cabin is the perfect place to relax and unwind. Relax and converse on the screened in back deck. Tell scary ghost stories around the fire pit. Cook those delicious hamburgers and hot dogs on the grill. Enjoy the amazing views of the Bluegrass and breathtaking stargazing from the overlook. Take a stroll throughout the woods.

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!

A Frame of Mind - near Red River Gorge KY

Escape to the Kentucky Rockies to this deluxe 2-bedroom, 1-bathroom tiny cabin near Red River Gorge. A Frame of Mind comfortably sleeps up to 4 guests and is located within 30 minutes of Natural Bridge State Park. You can find yourself relaxing on the beautiful deck while taking in all that nature has to offer or enjoying a cozy fire after a strenuous day of adventuring. This tiny cabin is exactly what your small group getaway needs when searching for an affordable getaway!

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.

Charming Downtown Apartment

Introducing a charming two bedroom, one bathroom apartment nestled in the heart of downtown Mt. Sterling, Kentucky. This meticulously preserved gem invites you to step back in time while enjoying modern comforts. Located within the historic Farmers National Bank building, the space exudes character. Take a stroll down Main Street to find a variety of great restaurant and shopping opportunities. Located within 35 miles of Lexington and the Red River Gorge.

Welcome to the Star Cottage!

The Star Cottage contains 3 bedrooms and 2 full baths. Two of the bedrooms have queen beds, with the 3rd having an adorable set of log bunkbeds and a twin size single bed. The living room contains two full couches and a recliner for plenty of room to stretch out and enjoy your stay. There is also a washer/dryer available.