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.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.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.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.485 Cromwell Way, photo 5

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 $143 / 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

270 Hill N Dale Dr

Lexington, Kentucky · 10 min to Keeneland

Relax in this spacious 5-bedroom Lexington retreat, just a short drive from downtown and UK. It’s perfect for families or groups with room for 12, high-speed internet, a hot tub, fire pit, and games, all while keeping things cozy and welcoming.

12
Guests
5
Bedrooms
7
Beds
2.0
Baths
from $145 / night · Book a stay
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.Pull two chairs up to the fire pit while the hot tub steams a few feet away — string lights overhead, the whole pergola built for exactly this kind of night.Step outside and you're basically off the grid — arborvitae hedges block the neighbors, hot tub and fire pit tucked into their own private pergola corner.Stretch out on your own leather sofa before bed — a king bed under the sloped ceiling, a bench at the foot for stacking your bags.270 Hill N Dale Dr, photo 5

More in Lexington

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 $150 / night · View
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
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 $175 / 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 $185 / 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
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
12
Guests
5
Bedrooms
6
Beds
4.5
Baths
from $185 / 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 $190 / 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 $195 / night · View
3141 Lamar Dr

3141 Lamar Dr

Lexington, Kentucky · 10 min to Keeneland
12
Guests
5
Bedrooms
7
Beds
3.5
Baths
from $214 / 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 $250 / night · View
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.

1934 Natchez Trl

Lexington, Kentucky · 10 min to Keeneland
10
Guests
4
Bedrooms
5
Beds
2.5
Baths
from $125 / 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 $150 / 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 · 6 min

The Lexington Nobody Tells You About: 6 Things Locals Do That Visitors Miss

Skip the brochure. How a six-generation Lexington family actually spends a weekend: horse farm tours, a French bakery, dawn at Keeneland, a hidden spring, pizza in a bourbon warehouse, and the city's newest park.

Lexington · 8 min

Where to Stay for Keeneland: A Local's Guide to Every Option

Where to stay for Keeneland, by area: the west side, downtown, Kenwick and Chevy Chase, Versailles, and what to do when Lexington is full. Hotels and whole houses, with race dates and ticket prices.

Lexington · 11 min

Large Group Vacation Rentals in Lexington, KY: What to Know Before You Book

Lexington caps rentals at 10 to 12 guests, so one house rarely sleeps a big group. How to book for 14+ people, plus Keeneland, Breeders' Cup and tour booking windows.

Win two nights on us

Join the list for a chance to win a free 2-night stay at a Sixgen home, with nights, cleaning and taxes on us. We draw a winner every quarter and choose the home and the dates.

No purchase necessary. Next drawing 31 March 2027. Official rules

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