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.

Guest favorite

Farm stay in Winchester

4.93 out of 5 average rating, 101 reviews

LenMar 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

R1,835 ZAR per night
Guest favorite

Apartment in Mount Sterling

4.94 out of 5 average rating, 48 reviews

Historic 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

R2,350 ZAR per night
Guest favorite

Home in Paris

4.85 out of 5 average rating, 34 reviews

Misfit 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

R2,453 ZAR per night

Popular amenities for Montgomery County vacation rentals

Other great vacation rentals in Montgomery County

Guest favorite

Barn in Paris

4.93 out of 5 average rating, 60 reviews

Horse & Flower Farm Barn Loft

Mar 15 – 20

R2,978 ZAR per night
Guest favorite

Cottage in Clay City

4.99 out of 5 average rating, 90 reviews

Scenic views, farm fun in peaceful modern cottage

Apr 27 – May 4

R2,445 ZAR per night
Guest favorite

Tiny home in Stanton

5.0 out of 5 average rating, 31 reviews

Tiny Cabin At The Pond

Aug 18 – 25

R2,819 ZAR per night
Guest favorite

Home in Morehead

5.0 out of 5 average rating, 26 reviews

Sunset Cottage

Mar 6 – 13

R2,422 ZAR per night
Guest favorite

Home in Irvine

5.0 out of 5 average rating, 41 reviews

Pauline's Paradise

Jul 20 – 27

R1,744 ZAR per night
Guest favorite

Cabin in Stanton

4.93 out of 5 average rating, 30 reviews

Red Door Cabin Four

Feb 6 – 13

R1,888 ZAR per night
Guest favorite

Cabin in Salt Lick

4.89 out of 5 average rating, 82 reviews

The Cedar Shack

Jul 26 – Aug 2

R1,647 ZAR per night
Guest favorite

Cabin in Stanton

4.97 out of 5 average rating, 29 reviews

Red Door Cabin Six

May 30 – Jun 6

R2,072 ZAR per night
Guest favorite

Cabin in Hillsboro

4.96 out of 5 average rating, 74 reviews

Beautiful Country Sunsets 2

Jan 25 – Feb 1

R1,528 ZAR per night
Guest favorite

Cabin in Irvine

4.95 out of 5 average rating, 57 reviews

Sunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!

Dec 9 – 16

R2,169 ZAR per night
Guest favorite

Condo in Paris

4.93 out of 5 average rating, 84 reviews

Paradise Inn B&B - Lover's Suite

May 17 – 24

R2,045 ZAR per night
Guest favorite

Home in Clay City

4.94 out of 5 average rating, 36 reviews

Happy Top Hideaway Red River Gorge

Dec 11 – 18

R2,503 ZAR per night