House holiday rentals in Kentucky

Find and book unique houses on Airbnb

Top-rated house rentals in Kentucky

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

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Guest favourite

Home in Stamping Ground

4.97 out of 5 average rating, 608 reviews

Buffalo Springs Distilling Company

On the Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one bedroom due to the size of the structure. Queen size bed in the bedroom. There’s also a Queen Air Mattress that can be utilized in a pinch for folks that are staying at least a week

28 Feb – 7 Mar

$214 SGD per night

Guest favourite

Home in Lexington

4.96 out of 5 average rating, 323 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

19–26 Jan

$248 SGD per night

Guest favourite

Home in New Hope

4.93 out of 5 average rating, 162 reviews

The Barrel House Bed & Breakfast

The Barrel House is in our 6th year of operation and originally we catered to "Bourbon enthusiasts". However, over these past 5 years, we have had so many guests stay with us for family vacations and reunions, bird watching, star gazing, history seeking, biking and touring as well as spirits! Whatever your reason to visit, you have EVERY reason to stay at the Barrel House. Our version of night life is cozying up to the fire pit with a good pour, good friends and a spectacular view of the stars.

7–14 Apr

$176 SGD per night

Guest favourite

Home in Berea

4.92 out of 5 average rating, 639 reviews

Berea Painter's Cottage

Eclectic, clean, comfortable cottage featuring original artwork, located in walking distance of Berea College Campus, Artisan Village/Old Town area, Art Galleries, Unique Shops, The Lot, Rebel Rebel, Nightjar, Sunhouse Craft, and Native Bagel. A short drive to the Pinnacles and Kayaking at Owsley Fork Lake. The location is great. A cozy patio in front of the home with a swing and a tree canopied deck in back that feels like being in a treehouse. Basic TV channels and high-speed internet.

6–13 May

$141 SGD per night

Guest favourite

Home in Harrodsburg

4.93 out of 5 average rating, 205 reviews

Kentucky Horse Farm Barndo On The Bourbon Trail

My place is close to Shaker Village, Old Fort Harrod State Park, Historic Beaumont Inn, Bright Leaf Golf Course, Pioneer Playhouse, Perryville Battlefield State Historic Site, Danville KY, Centre College. You’ll love my place because of the views, the location, the horses, the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Also close to Four Roses Distillery, Wild Turkey Distillery, Wilderness Trail & Buffalo Trace & Makers Mark

15–22 Sep

$140 SGD per night

Guest favourite

Home in Versailles

4.93 out of 5 average rating, 122 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

27 Mar – 3 Apr

$179 SGD per night

Guest favourite

Home in Springfield

4.98 out of 5 average rating, 535 reviews

Cabin Chic on Main

I invite you to take a step back in time while experiencing the comfort and appeal of today in the charming atmosphere of a mid-1800’s original log cabin right in town. It was the home to author Elizabeth Maddox Roberts. There is a large backyard complimented by a grazing hillside and a stream that separates the two. A truly unique setting. And, enjoy a large patio and fire pit to enhance your relaxation at the end of the day. I do not rent for local parties or gatherings.

5–12 Oct

$129 SGD per night

Guest favourite

Home in Grand Rivers

4.98 out of 5 average rating, 543 reviews

Seclusion with the Lake a step away....

It is one bedroom apartment in the basement of our home, with no cleaning fee because we want you to treat it as you would your home. There is a separate entrance and access to 26 acres of hills and trees. We have two horses on the property and feed from anywhere 3 to 15 deer each evening. We are 4.2 miles from I-24 and 7 miles from Kentucky lake, Patti's, Turtle Bay and the marina. Full kitchen available and beautiful sunsets. It is beautiful, words cannot do it justice.

12–19 Sep

$125 SGD per night

Guest favourite

Home in Winchester

4.91 out of 5 average rating, 676 reviews

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

8–15 Jul

$83 SGD per night

Guest favourite

Home in Raywick

5.0 out of 5 average rating, 167 reviews

Bourbon Trail Country Farmhouse

The Olde Farmhouse is secluded on 5.8 acres and is on the historic Bourbon Trail. The house has a master on the main floor with a queen bed connected to the bathroom. There is an upstairs sleeping space that accommodates one queen bed and two twin beds. Beautiful wrap around porch for your morning coffee enjoyment or evening relaxation. All that can be heard on this property are crickets and frogs with lovely sunsets.

5–12 Oct

$181 SGD per night

Guest favourite

Home in Bardstown

4.95 out of 5 average rating, 461 reviews

Creekview Farm: Bourbon, Horses, and Sunsets

On this beautiful 19 acre horse farm, you will enjoy beautiful sunrises and sunsets. You will have the country feel while only being 3.5 miles from downtown Bardstown. The airbnb apartment located in the front of the horse barn. It is located behind the main farm house which is a long term rental house. The horses, cats, goats, chickens, and dogs belong to the long term rental tenants.

27 Aug – 3 Sep

$177 SGD per night

Guest favourite

Home in Lewisburg

4.98 out of 5 average rating, 104 reviews

Charming Lakefront A-Frame with 4 Adult Kayaks

This charming A-Frame is your perfect lake getaway. Only a couple of blocks from the boat launch. Located on Lake Malone. Great fishing and boating right off the pier. Pier to park your boat and parking for your trailer and vehicles. Please bring your own beach towels. We have a strict no animal policy due to allergies . This property is not well suited to service animals.

12–19 Oct

$181 SGD per night