Holiday rentals with a pool in Nelson County

Spacious carriage house, heated pool all year!

This carriage house (1,150 sq.ft) is located on one of the most beautiful properties in the most beautiful small town in America. Located just minutes from downtown in the heart of Bourbon Country. Enjoy the year around pool and playground on the property! YES, SWIM ALL YEAR UNDER DOME. 2 adults + kids. Tree lined location close to restaurants, bars, shopping. apartment has a gorgeous interior, full kitchen, brand new pillow top bedding, new comfortable sofa bed. HD TV and internet on site.

Ticky's Cottage at Empire Estate

Enjoy all the amenities, such as an inground pool (May TBD-Labor Day, 8 a.m.-10 p.m.), 4 manicured acres to roam, volleyball/badminton court (8 a.m.-8 p.m.), fire pit/picnic area (8 a.m.-10 p.m.) next to a stream, horseshoes and more, all within 50 minutes of the major Bourbon Country distilleries. Amenities and lodging are for booked guests only. Visitors, children and pets are not allowed on the property at any time. This is a genuine Bourbon Country getaway spot with lots of fun minutes away.

Luxury Estate: Sauna, Spa, Bourbon Room, & Cinema!

Your Kentucky Dream Awaits: Kentucky’s Most Spectacular Sunset Views Private Bourbon Tasting Room Private Cinema +Poker Room + Billiard Lounge Stunning 16-ft Ceiling Living Room w/ wraparound sectional, bar & lounge Private Saltwater Pool + 6-Person Hot Tub + Handcrafted Barrel Sauna 6 Private Acres w/ stocked pond & fire pit for 12 ppl, perfectly positioned for sunset magic Grand Dining Deck w/ BBQ, built-in hot tub overlooking the estate Covered Gazebo w/ Bar Just 12 Min from Bardstown

Pickleball*Hot Tub*Pool*Bourbon Trail*Sleeps 16!

Welcome to the Cabin at Rams Run! This newly renovated 5-bed, 5 full-bath cozy cabin is the perfect resort for adult trips and families alike. Situated on top of a ridge just above the James B. Beam Distillery, the cabin is in a perfect location directly between the culture and attractions of Louisville, and the distilleries of Bardstown--the bourbon capital of the world! After touring the Kentucky countryside, enjoy the hot tub, game room with pool table, or the indoor pickleball court!

Bourbon Trail Pool&Hottub FUN-ZONE! GameRm! Fish!

This two-story country-side home is sure to keep you entertained while also having a relaxing vibe for your getaway. Nestled just off the Bourbon Trail, Makers Mark and historic Bardstown are just a short drive. Proximity to Louisville and Lexington is great too! Sitting on 3 acres, this home Features 4 bedrooms, 2 and a half bathrooms, WiFi/Cable, Pool Table, Ping Pong Table, Golden Tee Arcade Machine, and all amenities. In-ground Pool expected ready by late August!

Private 1000 sq ft 1-bedroom lower level apartment

Relax in this beautiful wooded setting in Bourbon Country less than 4 miles from I-65. Private entrance into freshly painted 1-bedroom unit with new kitchen and 9' ceilings. Perfectly located near 19 Bourbon Distilleries, 4 Wineries, Bernheim Forest, Knob Creek Gun Range, Churchill Downs and other exciting destinations. Jim Beam Distillery & Forest Edge Winery are 7 min away. There is a seasonal (shared) concrete patio, deck and pool available in the warmer months.

Bourbon Retreat • Hot Tub + Game

* Hot Tub + Firepit • End your day under Kentucky stars with bourbon & laughter * Speakeasy Game Room • Arcade, poker, pool & bar TVs for friendly competition * 5 Bedrooms • Space to unwind, swap stories & wake to peaceful farm views * 10 Min to Distilleries • Willett, Heaven Hill & Lux Row adventures nearby * Fully Stocked Kitchen • Cook, sip & connect over bourbon-inspired meals * Seasonal Pool • Opens spring–summer with serene country views & privacy

Country 1 bedroom guesthouse with heated pool

Angels Rest unique country getaway. In the heart of the Bourbon Trail. 5 miles from the historic Bardstown. Within 15 miles from 12 distilleries. 1 loft bedroom, full kitchen, large deck with outdoor eating area, heated pool with lounging area. Enjoy fishing we have a large pond bring your fishing pole. Very quiet and relaxing, get away from the city on our 20 acre retreat. Pool open seasonal.

Downtown Abode Your home away from home.

No cleaning fee ,Beautiful home in downtown Lebanon a prime location for visiting many locations on the Bourbon Trail or the Lincoln Heritage Trail. We are 60 miles from Louisville or Lexington and only 15 miles from Historic Makers Mark Distilery. Several of our guests have stated the downtown abode is the best Airbnb they have ever stayed in. As a added bonus we have no cleaning fee

The Rickhouse Retreat Curved Theater Screen • Golf

Discover The Rickhouse Retreat — a 3-level, 5-bedroom luxury home in Bardstown’s bourbon country. Designed for up to 10 guests, it features a private golf simulator, movie theater with sound system, tasting room lounge, indoor infrared sauna, and outdoor hot tub. Perfect for milestone celebrations or executive retreats, every space blends modern comfort with Kentucky’s timeless charm.

The Bluegrass Grand Estate: Bourbon Trail Luxury

Nestled in the heart of Bardstown, Kentucky—“The Most Beautiful Small Town in America”, The Bluegrass Grand Estate is a luxurious retreat, where heritage meets modern elegance. Inspired by the spirit of the Bourbon Trail and Kentucky’s legendary thoroughbred legacy, this estate offers a seamless blend of Southern charm, timeless sophistication, and warm hospitality.

Adorable one bedroom w/ fireplace. Bourbon trail

Keep it simple at this peaceful and centrally-located place along the bourbon trail .. Sit back and enjoy the view of the farm , cattle , and the sun that rises above the surrounding knobs. Listen to the birds as you have your morning coffee and the coyotes as you sit by the fire pit in the evening ..