SIXGEN STAYS

Vacation rentals in Lexington

Family-owned homes in the neighbourhoods, ten minutes to Keeneland and five to downtown dinner.

LexingtonBourbon TrailWilliamstownAsheville

17 homes in Lexington

17 family-owned homes in Lexington, sleeping 6 to 12, from $100 a night. 10 min to Keeneland. Every home is owned and managed by the Hillenmeyer family, and booking here adds no listing-site service fee.

01 / 17

485 Cromwell Way

Lexington, Kentucky · 10 min to Keeneland

Enjoy a beautifully renovated 4-bed, 2.5-bath Lexington home, your peaceful, pet- and kid-friendly retreat with a large backyard, game room, and space to relax and gather.

12
Guests
4
Bedrooms
5
Beds
2.5
Baths
from $135 / night · Book a stay
Pour the coffee, then hand off breakfast duty to whoever claims the island stool — four seats and brand-new appliances mean you'll actually want to cook together this trip.Rack 'em up and call next — the basement ping pong table turns into the real competition of the trip once you get a few rounds in.Kick your shoes off under the beams and let the fireplace do the talking — this is where the group ends up every single night, board game or not.Pull the car in and feel the whole trip start — plenty of driveway for everyone's vehicles and a front yard that says you've found the right house before you even reach the door.Claim the primary suite and let the king bed do exactly what it promises — this is the room where you'll finally pay off the trip's sleep debt.

02 / 17

1105 Kees Rd

Lexington, Kentucky · 10 min to Keeneland

Experience comfort and convenience in this updated 4-bedroom home featuring six high-quality memory-foam beds, a modern kitchen, and a bright, welcoming living room. With two bedrooms on each level, it’s ideal for families, groups, or work trips. Enjoy a spacious yard, fire up the BBQ,…

12
Guests
4
Bedrooms
5
Beds
2.0
Baths
from $145 / night · Book a stay
Relax in a spacious, light-filled living room featuring seating for up to 10 guests and a large smart TV. Contemporary décor, comfortable furnishings, and a warm, inviting atmosphere make it the perfect hub for gathering after a day of adventure.Welcome to our beautifully remodeled Airbnb kitchen, fully stocked for all your cooking needs. The modern design features sleek countertops and state-of-the-art appliances. Everything from the pots and pans to the spices are provided, making it easy to whip up a delicious meal.Classic brick home with great curb appeal — spacious driveway with room for the whole group to park up and settle in.The main-floor king bedroom — comfortable, bright, and steps from the kitchen. Modern decor, natural light, and the kind of rest that sets the tone for a great trip.This 1st-floor bathroom is the perfect place to unwind with its sleek design and bathtub-shower combo.

03 / 17

1934 Natchez Trl

Lexington, Kentucky · 10 min to Keeneland

Gather your people in the Gardenside neighborhood, just minutes from downtown Lexington. Sink into evenings on the spacious back deck, swap stories around the fire pit, and challenge cousins to a ping-pong rematch at the basement bar. Four real bedrooms, room for up to 12…

12
Guests
4
Bedrooms
5
Beds
2.5
Baths
from $145 / night · Book a stay
Kick off your stay by settling into this wide-open living space, where the sectional, fireplace, and flat-screen TV pull the whole group together for movie nights.Gather around the island while dinner comes together — this fully equipped white kitchen makes cooking for twelve feel effortless.Challenge the family to ping pong or pull up a bar stool for drinks — this basement hangout is built for competitive nights in.Step outside to the deck for morning coffee or evening drinks, with the real fire pit just steps away in the yard below.Unwind in the main-level king suite, where soft gray-andnavy tones and a private armchair nook make it easy to fully switch off.

More in Lexington

Pull into the driveway and feel the trip start right here — a wide covered porch and manicured lawn welcome your entire group home.

353 Owsley Ave

Lexington, Kentucky · 10 min to Keeneland
12
Guests
5
Bedrooms
6
Beds
3.5
Baths
from $170 / night · View
Pour the first cup of coffee at the island while everyone drifts in — this open kitchen is where your group lands the second they walk through the door, twelve people and nobody in the way.

687 Hill N Dale Rd

Lexington, Kentucky · 10 min to Keeneland
12
Guests
5
Bedrooms
6
Beds
3.0
Baths
from $173 / night · View
Pull in and feel the trip start — a crisp white farmhouse, a covered porch wide enough to greet the whole group, and fencing on both sides so the kids can run loose from minute one.

336 Owsley Ave

Lexington, Kentucky · 10 min to Keeneland
12
Guests
5
Bedrooms
6
Beds
3.5
Baths
from $185 / night · View
Slide into the hot tub as the sun sets behind the pergola — this is where day one of your trip ends and every day after starts.

668 Springridge Dr

Lexington, Kentucky · 10 min to Keeneland
12
Guests
6
Bedrooms
7
Beds
3.5
Baths
from $187 / night · View
Pull into the driveway and the whole group already knows this is the one — white farmhouse, black shutters, a private corner lot with room for five cars and everyone who's coming with you.

341 Sherman Ave

Lexington, Kentucky · 10 min to Keeneland
12
Guests
5
Bedrooms
6
Beds
4.5
Baths
from $191 / night · View
Kick your shoes off the second you walk in — the fireplace crackling, the whole group spilling from the kitchen into the couch, this is where twelve people actually fit in one room.

270 Hill N Dale Dr

Lexington, Kentucky · 10 min to Keeneland
12
Guests
5
Bedrooms
7
Beds
2.0
Baths
from $192 / night · View
Work on your short game on the private putting green - real turf in your own backyard means the golf trip starts the second you arrive.

468 N MLK

Lexington, Kentucky · 10 min to Keeneland
12
Guests
5
Bedrooms
7
Beds
3.0
Baths
from $206 / night · View
Slip into the private hot tub after dark — fire pit glowing, Adirondack chairs waiting, fenced yard all yours. This is the shot guests keep mentioning in their five-star reviews.

1810 Clays Mill Rd

Lexington, Kentucky · 10 min to Keeneland
12
Guests
5
Bedrooms
6
Beds
3.0
Baths
from $238 / night · View
3141 Lamar Dr

3141 Lamar Dr

Lexington, Kentucky · 10 min to Keeneland
12
Guests
5
Bedrooms
7
Beds
3.5
Baths
from $243 / night · View
Sink into the plush sofa beneath your soaring beamed ceilings — this vaulted living room, warmed by a fireplace, is where your whole group naturally gathers.

300 Sherman Ave

Lexington, Kentucky · 10 min to Keeneland
12
Guests
7
Bedrooms
10
Beds
6.5
Baths
from $275 / night · View
Step up to the hitting mat and take your swing — the Foresight launch monitor tracks every shot so your bragging rights are officially on the record.

340 Lincoln Ave

Lexington, Kentucky · 10 min to Keeneland
10
Guests
5
Bedrooms
6
Beds
4.5
Baths
from $218 / night · View
Twilight Craftsman exterior with a lit front porch and manicured lawn — your hero shot.

834 Melrose Ave

Lexington, Kentucky · 10 min to Keeneland
8
Guests
3
Bedrooms
4
Beds
2.5
Baths
from $202 / night · View
Relax in style with our smart TV and comfortable living room - the perfect spot to unwind after a day of exploring!

617 Stratford Dr

Lexington, Kentucky · 10 min to Keeneland
6
Guests
2
Bedrooms
3
Beds
1.0
Baths
from $100 / night · View
Step inside this beautifully designed home, where comfort meets style. With warm tones, modern finishes, and spacious living areas, it’s the perfect retreat for families or groups seeking a memorable stay.

720 W Short St

Lexington, Kentucky · 10 min to Keeneland
6
Guests
3
Bedrooms
3
Beds
2.5
Baths
from $175 / night · View

Where they are

Prices on the map change with your dates.

Keep reading

Guides in Lexington from the people who live here.

Lexington · 3 min

The Ultimate Guide to Visiting Keeneland

Race dates, what to wear, parking, tailgating, and where your group should stay for a Keeneland weekend.

Lexington · 2 min

Best Things to Do in Lexington, Kentucky

Horse farms, Keeneland, bourbon, downtown restaurants, and family favorites from the people who live here.

Family travel · 3 min

Planning a Kentucky Family Vacation: Where to Go & Stay

The Horse Park, the Ark Encounter, and easy home bases for families visiting Kentucky with kids of every age.

Ten percent off your first stay

Join the list for first look at open Keeneland weekends, Ark holiday weeks and leaf season.

26
Homes
4.9
1,240 reviews
T+L
Top 10 · Lexington
6
Generations