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Vacation rentals in Montgomery County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montgomery County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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
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
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

Other great vacation rentals in Montgomery County

Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
$156 per night
Cabin in Stanton
Elderberry Cabin w/ Hot Tub near Red River Gorge
$121 per night
Home in Winchester
Cozy Cottage
$60 per night
Cabin in Slade
Fireside, Extraordinary Couples Cabin
$114 per night
Cabin in Stanton
Hot Tub, WiFi, Netflix and Cable, Close to RRG!
$140 per night
Cabin in Pine Ridge
Cliffside Cabin 2 King ALCOVES, Hot Tub, Cargo Net
$226 per night
Home in Stanton
Hot tub, WIFI/NFLX, Incredible View, close to RRG
$125 per night
Guesthouse in Stanton
Robbie’s Rest: Amazing Mountaintop Sunrises
$150 per night
Place to stay in Stanton
Cemetery Gatehouse w/ Hot Tub and WIFI - RRG
$105 per night
Apartment in Hillsboro
Beautiful Country Sunsets I
$78 per night
Loft in Mount Sterling
One Bedroom apartment with full kitchen
$79 per night
Apartment in Mount Sterling
Historic 2-Bedroom Apartment in Downtown
$110 per night

Destinations to explore