Bourbon Trail Estate | 6BR | Pickleball | Hot Tub
Bourbon Trail Estate | 6BR | Pickleball | Hot Tub
Expansive covered outdoor living space featuring deep-seat sectional lounge chairs, egg swings, and outdoor dining.
Bourbon Trail Estate | 6BR | Pickleball | Hot Tub
Bourbon Trail Estate | 6BR | Pickleball | Hot Tub

Bourbon Trail Estate | 6BR | Pickleball | Hot Tub

6 bedrooms·4½ baths
Chaplin • Kentucky

$ 2.004,42 USD totaal voor 3 nachten

15–18 nov 2026

Prather Ridge Estate | 3BR | Bourbon + Pickleball
Prather Ridge Estate | 3BR | Bourbon + Pickleball
Prather Ridge Estate | 3BR | Bourbon + Pickleball
Prather Ridge Estate | 3BR | Bourbon + Pickleball
Prather Ridge Estate | 3BR | Bourbon + Pickleball

Prather Ridge Estate | 3BR | Bourbon + Pickleball

3 bedrooms·2½ baths
Chaplin • Kentucky

$ 1.102,50 USD totaal voor 3 nachten

16–19 nov 2026

So much to see, do and enjoy at The Ridge
Hot tub, suana, fire pit, chipping green, backyard games, all perched atop 5 acres of Kentucky Bluegrass
Stylish guest bedroom with statement wall paneling, plush bedding, and peaceful countryside views
Spacious open living area perfect for group conversations, enjoying the fire (electric) or simply taking a nap
Your own bourbon-inspired hangout with a custom bar, pool table, plush seating, and moody Southern style — perfect for late-night pours and friendly competition

The Ridge: 6BR • 100" TV • Hot Tub • Speakeasy

6 bedrooms·3 baths
Waddy • Kentucky

$ 2.087,08 USD $ 1.654,10 USD totaal voor 3 nachten

21–24 nov 2026

Secluded・Speakeasy・Sauna・Cigar Shed・Hot Tub
Welcome to The Bourbon Exhale—a beautifully renovated farmhouse where rustic charm meets refined comfort. Set on over an acre of peaceful Kentucky countryside, this inviting retreat offers privacy, style & a warm welcome from the moment you arrive.
Gather, sip, and relax after a day on the Bourbon Trail—the covered deck features cozy seating around the fire, an outdoor dining area, a bubbling hot tub, and a barrel sauna made for unwinding in good company.
Kick back or turn in—this stylish basement sofa easily transforms into a comfy sleeper.
Stretch out on the luxe king bed wrapped in organic cotton Quince linen, then wake to gentle light and peaceful views that make sleeping in irresistible.

Secluded・Speakeasy・Sauna・Cigar Shed・Hot Tub

3 bedrooms·3 baths
Lawrenceburg • Kentucky
5(30 reviews)

$ 1.252,90 USD totaal voor 3 nachten

16–19 nov 2026

Vintage Bourbon Haven
Vintage Bourbon Haven
Vintage Bourbon Haven
Vintage Bourbon Haven
Vintage Bourbon Haven

Vintage Bourbon Haven

3 bedrooms·2½ baths
Springfield • Kentucky
5(69 reviews)
$140 – $270/ nacht(excl. kosten & belastingen)
The Angels Share, Bardstown on Kentucky Bourbon Trail
The Angels Share, Bardstown on Kentucky Bourbon Trail
The Angels Share, Bardstown on Kentucky Bourbon Trail
And they're off! If you feel like you can't run another furlong on the bourbon trail, have no fear! Our comfortable Kentucky Thoroughbred room welcomes you to bed down for the evening.
The Angels Share, Bardstown on Kentucky Bourbon Trail

The Angels Share, Bardstown on Kentucky Bourbon Trail

4 bedrooms·1 bath
Bardstown • Kentucky

$ 456,88 USD totaal voor 3 nachten

15–18 nov 2026

Deck+Grill | View | 4BR | Wild Turkey | Four Roses
Deck+Grill | View | 4BR | Wild Turkey | Four Roses
Deck+Grill | View | 4BR | Wild Turkey | Four Roses
Deck+Grill | View | 4BR | Wild Turkey | Four Roses
Deck+Grill | View | 4BR | Wild Turkey | Four Roses

Deck+Grill | View | 4BR | Wild Turkey | Four Roses

4 bedrooms·2½ baths
Lawrenceburg • Kentucky

$ 740,00 USD totaal voor 3 nachten

15–18 nov 2026

Enjoy the year round hot tub while taking in the serenity of the lake.
KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!
Private kitchen
King bed in master with view of lake & balcony with seating.
Living area

KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!

3 bedrooms·1 bath
Lawrenceburg • Kentucky

$ 822,70 USD totaal voor 3 nachten

15–18 nov 2026

Modern Bourbon Cottage
Modern Bourbon Cottage
Modern Bourbon Cottage
Modern Bourbon Cottage
Modern Bourbon Cottage

Modern Bourbon Cottage

1 bedroom·1 bath
Lawrenceburg • Kentucky

$ 561,00 USD totaal voor 3 nachten

20–23 nov 2026

Modern Home on the Bourbon Trail
Modern Home on the Bourbon Trail
Modern Home on the Bourbon Trail
Modern Home on the Bourbon Trail
Modern Home on the Bourbon Trail

Modern Home on the Bourbon Trail

1 bedroom·1 bath
Lawrenceburg • Kentucky

$ 554,00 USD totaal voor 3 nachten

22–25 nov 2026

Outside patio swing/firepit area with pavilion.
Living room.
Stubborn German House of Bourbon, Lawrenceburg, KY
Living room.
Fully stocked kitchen with plates/utensils/serving utensils, pots/pans, coffee maker and supplies.

Stubborn German House of Bourbon, Lawrenceburg, KY

3 bedrooms·2 baths
Lawrenceburg • Kentucky
5(30 reviews)

$ 706,20 USD totaal voor 3 nachten

15–18 nov 2026

Our main level open concept layout is optimal for groups to always be together and enjoy each other's company.
Views of the Kentucky rolling hills from our barrel sauna.
The large climate-controlled game room/lounge is packed to keep everyone busy before or after your daily activities. Pictured here are the dry bar w/ mini-fridge, billiards table, board games (hung on the wall) and comfortable seating.
Guests can enjoy both a wood fire pit and a gas fire pit with dedicated seating, leaving options available if there is inclement weather. Wood is provided by the hosts!
We've supplied our gym with high-end equipment. Our weight-stacked functional trainer comes equipped with multiple attachments and various pull-up grips. The bench is adjustable and we provide kettlebells, dumbbells, a yoga mat, and a Roku TV.

4BR Bourbon Trail | Sauna Hot Tub Fire Pit Gym

4 bedrooms·2½ baths
Shelbyville • Kentucky

$ 1.357,20 USD totaal voor 3 nachten

28 nov – 1 dec 2026

River & Rye image 1
River & Rye image 2
River & Rye image 3
River & Rye image 8
River & Rye image 11

River & Rye

2 bedrooms·2 baths
Frankfort • Kentucky

$ 965,00 USD totaal voor 3 nachten

21–24 nov 2026

1920s Bourbon House | Fireplace | Buffalo Trace
1920s Bourbon House | Fireplace | Buffalo Trace
Dining Room: A stylish retreat with a dramatic chandelier and vibrant green walls for unforgettable meals!
Living Room Retreat: Dive into stylish decor with a sleek fireplace and Frankie the Stag with all of his charm!
Charming Bedroom: Enjoy a blend of modern comfort and equestrian vibes in this bedroom with stylish fan light fixture

1920s Bourbon House | Fireplace | Buffalo Trace

3 bedrooms·1½ baths
Frankfort • Kentucky

$ 475,96 USD totaal voor 3 nachten

15–18 nov 2026

Hot Tub Games Firepit Historic Luxe Bourbon Trail
Stay productive and relaxed with a dedicated workspace featuring a leather office chair and a cozy corner swivel chair, perfect for work or unwinding.
Our favorite space in the house features an arcade, a record player, cards, a poker set, and various games, all complemented by a bartender kit and glassware for a complete entertainment experience.
From the basics to the extras, we've got you covered! Fridge, electric stovetop, oven, dishwasher, microwave, toaster, crockpot, blender, hand mixer
Challenge friends and family on our Pac-Man arcade, perfect for all ages. Relive memories or share the thrill of classic gaming during your stay!

Hot Tub Games Firepit Historic Luxe Bourbon Trail

3 bedrooms·2½ baths
Frankfort • Kentucky
4.98(49 reviews)

$ 1.350,18 USD totaal voor 3 nachten

15–18 nov 2026

Garden on Capital-Bourbon & Horse Country
Quiet and charming home walking distance to so much!
Garden on Capital-Bourbon & Horse Country
Garden on Capital-Bourbon & Horse Country
Garden on Capital-Bourbon & Horse Country

Garden on Capital-Bourbon & Horse Country

2 bedrooms·1 bath
Frankfort • Kentucky

$ 493,75 USD totaal voor 3 nachten

15–18 nov 2026

Step into a vibrant and stylish kitchen that exudes coolness, featuring a contemporary design that is sure to impress.
This freestanding masterpiece is a celebration of design, its smooth porcelain surface adorned with gleaming, polished chrome fixtures that harken back to a bygone era.
Our bedroom, adorned with pristine white sheets, is a serene oasis where tranquility and comfort merge into a haven of restful reprieve.
Experience the epitome of comfort with a sleep-worthy sofa that offers both relaxation and a cozy chilling experience.
Loft on Capital - Ideally located to Distilleries

Loft on Capital - Ideally located to Distilleries

1 bedroom·1 bath
Frankfort • Kentucky

$ 432,25 USD totaal voor 3 nachten

29 nov – 2 dec 2026

At the rear is the Carriage House. The door on the left leads to the Loft, while the door on the right provides access to the Garden on the lower level. Escape to the Bourbon Trail and stay in the perfect spot for your next group trip.
GARDEN - Whether you're lounging with loved ones or enjoying a quiet moment alone, our large sofa provides the perfect backdrop for cherished memories and cozy conversations.
Bourbon Trio - 3 distinct units
Bourbon Trio - 3 distinct units
The loft - your private haven, boasting a queen-sized bed tucked away in its own cozy bedroom sanctuary.

Bourbon Trio - 3 distinct units

4 bedrooms·3 baths
Frankfort • Kentucky

$ 1.998,20 USD totaal voor 3 nachten

10–13 dec 2026

Experience the essence of comfort distilled and encapsulated within the embrace of a single, impeccably designed chair, promising a haven of relaxation and contentment like no other.
Unveil a small, yet comprehensively outfitted kitchen space, perfectly suited for the culinary enthusiast, providing all the necessary tools and amenities to effortlessly prepare and savor complete, gourmet meals.
Enter a haven of comfort and leisure with a bed that beckons you to rest, accompanied by a generously proportioned television that ensures an exceptional and immersive relaxation experience that exceeds your expectations.
Elevate the ambiance of our living space with a chic and practical touch, courtesy of a stylish accent table that infuses character and coolness into the overall design and always some goodies for arrival.
Carriage on Capital near Distilleries & Downtown

Carriage on Capital near Distilleries & Downtown

1 bedroom·1 bath
Frankfort • Kentucky

$ 352,95 USD totaal voor 3 nachten

15–18 nov 2026

2bd Bourbon Trail Cottage Fenced Yard
2bd Bourbon Trail Cottage Fenced Yard
2bd Bourbon Trail Cottage Fenced Yard
2bd Bourbon Trail Cottage Fenced Yard
2bd Bourbon Trail Cottage Fenced Yard

2bd Bourbon Trail Cottage Fenced Yard

2 bedrooms·2 baths
Frankfort • Kentucky

$ 476,00 USD totaal voor 3 nachten

15–18 nov 2026