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.
Farm stay in Winchester
4.93 out of 5 average rating, 101 reviewsLenMar Farm Country Stay near Lexington KY
Farm stay in the heart of the Kentucky Bluegrass 20 min from the Kentucky Horse Park and downtown Lexington. 30 min to Keeneland. 45 min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, and butlers pantry with coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.
Jun 6 – 13
Apartment in Mount Sterling
4.94 out of 5 average rating, 48 reviewsHistoric 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.
Aug 21 – 28
Home in Paris
4.85 out of 5 average rating, 34 reviewsMisfit Farm
Need to get away? Misfit Farm sits 700’ from the road and offers a newly renovated 3 bedroom Airbnb with a 10’ x 70’ covered porch & a fire pit. There is a spacious kitchen & dining area for family meals and a theatre room to enjoy a movie. Two bedrooms have queen beds and one a twin daybed with a trundle underneath. 6 guests can make this a home base for visiting local farms, horse events and bourbon trails. We are just 40 minutes from Lexington where you can enjoy Rupp Arena & Keeneland.
Nov 8 – 15
Vacation rentals for every style
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Popular amenities for Montgomery County vacation rentals
Other great vacation rentals in Montgomery County
Barn in Paris
4.93 out of 5 average rating, 60 reviewsHorse & Flower Farm Barn Loft
Mar 15 – 20
Cottage in Clay City
4.99 out of 5 average rating, 90 reviewsScenic views, farm fun in peaceful modern cottage
Apr 27 – May 4
Tiny home in Stanton
5.0 out of 5 average rating, 31 reviewsTiny Cabin At The Pond
Aug 18 – 25
Home in Morehead
5.0 out of 5 average rating, 26 reviewsSunset Cottage
Mar 6 – 13
Home in Irvine
5.0 out of 5 average rating, 41 reviewsPauline's Paradise
Jul 20 – 27
Cabin in Stanton
4.93 out of 5 average rating, 30 reviewsRed Door Cabin Four
Feb 6 – 13
Cabin in Salt Lick
4.89 out of 5 average rating, 82 reviewsThe Cedar Shack
Jul 26 – Aug 2
Cabin in Stanton
4.97 out of 5 average rating, 29 reviewsRed Door Cabin Six
May 30 – Jun 6
Cabin in Hillsboro
4.96 out of 5 average rating, 74 reviewsBeautiful Country Sunsets 2
Jan 25 – Feb 1
Cabin in Irvine
4.95 out of 5 average rating, 57 reviewsSunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!
Dec 9 – 16
Condo in Paris
4.93 out of 5 average rating, 84 reviewsParadise Inn B&B - Lover's Suite
May 17 – 24
Home in Clay City
4.94 out of 5 average rating, 36 reviewsHappy Top Hideaway Red River Gorge
Dec 11 – 18
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