Vacation rentals in Montgomery County

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Top-rated vacation rentals in Montgomery County

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

Guest favorite
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!
Dec 20 – 27
$70 per night
4.95 out of 5 average rating, 129 reviews
Guest favorite
Guesthouse in Winchester
Carriage House on the Park
Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.
Apr 17 – 24
$56 per night
4.95 out of 5 average rating, 150 reviews
Guest favorite
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.
Jun 18 – 25
$67 per night
4.98 out of 5 average rating, 170 reviews

Popular amenities for Montgomery County vacation rentals

Other great vacation rentals in Montgomery County

Guest favorite
Farm stay in Carlisle
Hilltop Retreat at Wendt’s Wildlife Adventure
Jan 28 – Feb 4
$135 per night
4.99 out of 5 average rating, 117 reviews
Superhost
Treehouse in Stanton
PRIVATE romantic TREEHOUSE w/AC! ★ The Lions Lair
Jul 19 – 26
$179 per night
4.89 out of 5 average rating, 541 reviews
Guest favorite
Guesthouse in Pine Ridge
Family Guest House-near Red River Gorge&MuirValley
Nov 21 – 28
$84 per night
4.99 out of 5 average rating, 318 reviews
Guest favorite
Cabin in Pine Ridge
Cliffside Romantic Retreat LOVE
Jan 2 – 9
$253 per night
4.98 out of 5 average rating, 111 reviews
Guest favorite
Apartment in Mount Sterling
Historic 2-Bedroom Apartment in Downtown
Apr 30 – May 7
$96 per night
4.94 out of 5 average rating, 48 reviews
Guest favorite
Loft in Mount Sterling
Downtown Loft Apartment, Relaxing Retreat
Mar 15 – 22
$72 per night
4.92 out of 5 average rating, 26 reviews
Guest favorite
Farm stay in Winchester
Tiny Farm Cottage *Comfy King*DT Winchester 5 min.
Mar 2 – 9
$70 per night
5.0 out of 5 average rating, 50 reviews
Superhost
Place to stay in Sharpsburg
Away From It All! Beautiful 1-bdrm. In the country
Aug 12 – 19
$98 per night
4.89 out of 5 average rating, 35 reviews
Guest favorite
Tiny home in Stanton
Tiny Cabin At The Pond
Apr 10 – 17
$86 per night
5.0 out of 5 average rating, 24 reviews
Guest favorite
Barn in Paris
Horse & Flower Farm Barn Loft
Feb 23 – 28
$136 per night
4.93 out of 5 average rating, 58 reviews
Guest favorite
Cabin in Salt Lick
The Cedar Shack
Nov 14 – 21
$76 per night
4.9 out of 5 average rating, 78 reviews
Guest favorite
Home in Mount Sterling
High Street Hideaway home atmosphere for relaxing
Apr 10 – 17
$142 per night
5.0 out of 5 average rating, 48 reviews

Destinations to explore