Vacation rentals in Montgomery County

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Top-rated vacation rentals in Montgomery County

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Superhost

Tiny home in Powell County

Hot Tub! Tiny Hūs Retreat in the Woods

Enjoy your own slice of the Red River Gorge in a brand new, unique, cozy tiny house. Soak in the brand new hot tub after enjoying the beauty of “The Gorge,” just a short 15 min drive to the Natural Bridge! Feel immersed in the outdoors with the sounds of nature, tons of natural light, and gentle rain on a metal roof. Roast marshmallows at the fire pit, grill food at the charcoal grill, then take a nap in the 2-person hammock before retiring in the loft on the comfortable queen sized bed.

$100 per night

Superhost

Home in Mount Sterling

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!

$79 per night

Superhost

Guesthouse in Winchester

Escape and unwind in the country

Relax and unwind in the country! Close to Lexington, Red River Gorge, Pilot Knob and Natural Bridge with easy access to the Mountain Parkway. We now have Wi-Fi!! Pets are welcome but we request that dogs are either crated or not left unattended. There is a $25 pet cleaning fee. Our guest house has a fully equipped kitchen, washer/dryer, queen size Sleep Number Bed, queen size sleeper sofa, and patio with gas grill. An air mattress is available by request.

$85 per night