Vacation rentals with a pool in Nelson County

#1 Bourbon Trail POOL&GAME ZONE! Keenland! Hottub!

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! Amenities include a newly constructed fenced in Inground Pool(open Mid March- end October),WiFi/DirecTV, Pool Table, Ping Pong Table, and GoldenTeeArcadeMachine!

Location · Family · Hot tub

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.

Location · Family · Beach

Triple Crown Estate | Bourbon Room | Spa | Pool

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

Family · Location · Grill

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!

Family · Location · Decor

Missy’s unique stays on the bourbon trail .

Welcome to this funky and eccentric property that sits on 72 acres of luscious farmland in the heart of Kentucky, situated along the bourbon trail .. Previously “Missy’s café ) now turned it into a country getaway for family, Friends or sweethearts .. it is set up for intimate events (extra) or just a nice quiet stay .. it has a beautiful view of the farm and surrounding knobs.. not to far away from civilization, but far enough too get away and enjoy nature

Location · Family · Indoor spaces

Rickhouse Retreat | Golf Sim*Massage Chairs*Sauna+

Welcome to The Rickhouse Retreat! Nestled on 6 private acres in the heart of Kentucky Bourbon Country, The Rickhouse Retreat is a luxury getaway designed for unforgettable family vacations, bourbon trail adventures, golf trips, and relaxing weekends with friends. From the hidden speakeasy tucked behind a Maker’s Mark-inspired door to the private golf simulator and spa retreat, every detail has been thoughtfully curated to create a one-of-a-kind experience.

Family · Location · Hospitality

Speakeasy Game Barn • Hot Tub • Bourbon Trail

🥃 Holidays for ten on 7 quiet acres, with a game barn for the cousins 🚗 11 min to downtown Bardstown, five distilleries within 20 min. Parking for 6. 🛏 Sleeps 10 · 5 bedrooms · 7 beds · 3.5 baths · one table seats all 10 ✨ Kitchen stocked for a full holiday dinner, with four more seats at the island ✨ Year-round hot tub, fire pit under a lit pergola, fireplace in the living room 📅 Built for holiday weeks and bourbon weekends. Save it to your wishlist.

Location · Family · Indoor spaces

Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub

Relax with the whole family at our newly remodeled home with modern finishes in a secluded country setting. Just minutes from the distilleries, downtown Bardstown, Taylorsville Lake, Keeneland, Lexington, Churchill Downs and Louisville makes this the perfect location for enjoying some of the best that KY has to offer. After a long day of tours and tastings come soak in the hot tub or sit around the fire enjoying the hilltop country views.

Family · Value · Amenities

Ticky's Cottage at Empire Estate

Visitors, children and pets are not allowed on the property at any time. Booked adult guests enjoy all the amenities, such as an inground pool (May-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 adult guests only.

Value · Family · Kitchen

Downtown Abode Your home away from home.

Our prices now include Air B&B service fee. 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

Value · Family · Sleep quality

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.

Location · Layout · Quiet

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.

Family · Value · Getting around