House holiday rentals in Anderson County

A charming backyard features a spacious patio area with a BBQ grill and seating under a sunshade. Lush green grass surrounds the patio, enhancing the outdoor setting. The home is painted in a deep blue, complemented by a colorful sunset creating a serene backdrop.

4.83 out of 5 average rating, 109 reviews

Bourbon Trail/8 mins to distilleries/Fenced Yard

Nestled on a well-manicured and expansive 0.24-acre lot, this pet-friendly, 3-bedroom home presents a tantalizing adventure along the famed Bourbon Trail. An effortless 10 minute walk places you in downtown Lawrenceburg, while the property itself offers a private fenced backyard ripe for enjoyment – featuring a BBQ grill for the best outdoor cookouts & patio furniture. Inside, 1584 sq. feet of space awaits, boasting an HDTV for your viewing pleasure and high speed Wi-Fi! IG: Careybluehouseonmain

A modern living room features a dark sectional sofa accompanied by two light-colored armchairs. A natural woven rug covers the floor, and a small wooden coffee table sits in the center. Greenery from a potted plant adds a touch of nature, complemented by soft lighting from a floor lamp.

4.87 out of 5 average rating, 166 reviews

The Homestead| Downtown| Near Bourbon Trail

The Homestead: this newly renovated home is stylish and centrally located. Situated in the heart of Downtown Lawrenceburg, just minutes from local shops, the county park, and a short drive to several Bourbon Distilleries! This home is great for groups and families looking to get away- with 3 beds and a pull out couch to accommodate your party's size. Upon entry you'll find a fully stocked kitchen with a large island for meal prep, a charming living room with Smart TV tech, and a fire pit. Cheers

Top Guest favourite

The exterior of a modern cottage is displayed, featuring a gray wood-paneled facade, a sloped roof, and a welcoming front entrance. A wooden staircase leads up to the porch, where inviting seating arrangements can be seen. Lush greenery surrounds the home, enhancing the tranquil setting.

4.97 out of 5 average rating, 164 reviews

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

Top Guest favourite

The home is nestled amidst a backdrop of gently rolling hills, framed by trees showcasing autumn foliage. A welcoming front porch is visible, accompanied by a small staircase leading to the entrance. Large windows allow natural light to filter into the living space.

Home in Versailles

5 out of 5 average rating, 115 reviews

Birdsong Valley on Bourbon Trail

Great central location on Bourbon Trail. Close to Lexington, airport, Keeneland, Ride the Rails, Horse Park, Shakertown, many other attractions. You will love our 3 bedroom charming home on 2.2 beautiful acres in peaceful community. Perfect for couples, friends, families, singles to explore distilleries, horse farms, quaint small towns of Versailles, Midway, Lawrenceburg, country backroads, much more. OR relax, enjoy nature, butterflies, birds, deer. Let us make lodging highlight of your visit.

A single-story home with a light exterior, featuring a welcoming front porch with white railings. Lush green grass surrounds the property, while trees provide a natural backdrop. The driveway leads up to the entrance, offering convenient access.

5 out of 5 average rating, 9 reviews

Peaceful Retreat on the Bourbon Trail

Relax with the whole family at this peaceful place to stay. Modest and affordable, this 3-bedroom, 2-bath home is the perfect stop for travelers exploring Kentucky’s Bourbon Trail and nearby attractions. Enjoy a fully equipped kitchen, satellite TV, WiFi, and washer/dryer. With ample parking, it’s a great fit for families, friends, or couples traveling together. Our goal is to make you feel at home and we're happy to help with anything you need during your stay. No pets over 25lbs inside home.

The image showcases a cozy barrel sauna with a large window offering views of the surrounding greenery. A speakeasy game room is visible, highlighted by decorative neon art. An outdoor firepit area features seating around a glowing campfire, with string lights adding ambiance. A wooden hot tub stands ready for use, adding to the relaxing atmosphere.

5 out of 5 average rating, 18 reviews

Secluded Bourbon Trail Retreat • Hot Tub & Sauna

Welcome to The Bourbon Exhale by Topaz Stays—your professionally-designed escape along Kentucky’s iconic Bourbon Trail. This peaceful country home blends rustic charm w/modern luxury, including a private hot tub, barrel sauna, speakeasy game room & cigar lounge. Located near Wild Turkey, Four Roses & more, it’s the perfect base for a distillery getaway. *Wild Turkey Distillery (11 miles) *Four Roses Distillery (13 miles) *Downtown Lawrenceburg (8 miles) *Rail Explorers (17 miles)

A brick house with a gabled roof is set in a grassy yard. The front features a central entrance with a circular window, flanked by two symmetrical sections. Black chairs are visible on the front porch, and bordered flower beds add greenery around the foundation.

4.99 out of 5 average rating, 107 reviews

Bourbon Trail*HotTub*Dog friendly*3BR*4 beds

A centrally located 3 bed 2 bath updated house in a family friendly neighborhood with a hot tub near downtown Lawrenceburg! Less than 10 minutes to Wild Turkey and Four Roses. Dogs Allowed! This rental has everything you need and proximity to Keeneland, multiple Bourbon Trail distilleries, UK athletics, Lexington and Frankfort! It is the perfect location for couples or families (and their 4-legged friends) looking to spend some time enjoying bourbon, horse racing, and all things Kentucky.

A charming white house is framed by well-maintained landscaping, featuring a pathway leading to the entrance. The porch is accentuated by wooden railings and steps, while a small tree provides shade beside the house. The driveway runs alongside the property.

4.93 out of 5 average rating, 57 reviews

Double Shot on Main 2 Bed/2 Bath - KY Bourbon Trl

Come to this central KY home for bourbon, wine, horses, sports, etc. but stay for the in-house fun that includes a game room. It is ideal for double date getaways, friend trips or couples. Located within 10 mins of Wild Turkey, Four Roses, 2 craft distilleries, 2 wineries, and a golf course. Within 1 hour drive to the most desired KY Bourbon Trail distilleries, several breweries and interesting cities such as Louisville, Bardstown, Frankfort and Lexington. Choose your fun and Book Now!

An outdoor seating area features plush, wicker couches and a wooden coffee table, situated under a covered deck. A hot tub bubbles nearby, with peaceful lake views in the background. String lights create a soft illumination, enhancing the inviting atmosphere of the space.

4.91 out of 5 average rating, 53 reviews

Lakefront. Boat Dock. Private Bar. Hot Tub

Escape to a unique lakefront retreat with a personal dock, perfect for relaxation and recreation. Enjoy the serene setting with a private firepit, BBQ, and pizza oven for cozy nights in. The charming horse jockey theme adds character to every room, creating an inviting atmosphere. Whether you're unwinding by the water, savoring a homemade pizza, or enjoying a drink at the bar, this getaway offers a memorable experience in a one-of-a-kind setting. Ideal for couples or small groups.

Top Guest favourite

A covered patio is presented with a round table and four chairs, surrounded by flower pots. The space is enclosed by brick walls, with multiple large windows providing natural light. A well-maintained lawn offers a peaceful outdoor environment.

4.92 out of 5 average rating, 93 reviews

Comfort in the Bluegrass

Comfort in the Bluegrass is a very clean, home nestled in the heart of bourbon and horse country. If it’s a little R&R you’re after, or entertainment…. This is the perfect location for either! We sit in a beautiful 1.6 acres located in a quiet, peaceful area in Anderson county. You can choose to relax with your friends or family by the fire pit, or tour one (or several) of the many sites around here! We are in between Lexington and Louisville, and only a few miles from Frankfort.

A light-filled living area features a tufted beige sofa flanked by two white chairs. A vintage-style trunk serves as the coffee table, while wall art of horses adds a subtle touch of elegance. Light curtains frame the windows, enhancing the space's openness.

4.91 out of 5 average rating, 284 reviews

Four Roses/ Wild Turkey/HOT TUB/3 acres

Welcome to Lawrenceburg, KY! You can't get any better of a location than this home! 3 mins to the Bluegrass Pkwy, not far from the most sought after bourbon distilleries, Lexington, Versailles, Bardstown, Shelbyville and just under an hour from Louisville! You'll love the super comfy queen beds, wood burning stove, fire pit, HOT TUB, and 3 acres of privacy on a hill. Enjoy this beautifully updated farmhouse right in bourbon and horse country!

The exterior of a charming brick home is displayed, featuring a well-maintained lawn with neatly trimmed hedges. The inviting front porch is highlighted by a blue door and illuminated by soft lighting as dusk approaches.