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Holiday houses in Stamping Ground

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Top-rated holiday rentals in Stamping Ground

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A rustic cabin is nestled among trees, featuring a well-lit entryway and a front deck with two wooden lounge chairs. Soft evening light spills through the windows, creating a welcoming atmosphere. Stone stepping stones lead towards the doorway, enhancing the natural setting.
Cabin in Lawrenceburg
4.98 out of 5 average rating, 246 reviews

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

Top Guest favourite
A private entrance is framed by trees displaying vibrant autumn foliage, adding bursts of red and orange. A gravel driveway leads toward a gated entrance, while fallen leaves create a colorful carpet along the pathway. Clear blue skies provide a bright backdrop.
Home in Lexington
4.95 out of 5 average rating, 398 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

Top Guest favourite
A paved driveway stretches into the distance, flanked by lush green grass and a large tree. Wooden fencing borders the property, offering views of rolling hills and a colorful sunset sky above.
Farm stay in Frankfort
4.99 out of 5 average rating, 159 reviews

The Cottage at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Restored log home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites & horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant & Bourbon Bar. Scenic horse farms (ASHFORD, AIRDRIE, WINSTAR). Convenient to KEENELAND, KY HORSE PARK, Versailles, Midway, Frankfort, Lexington, Louisville! Hike, bike, fish, wildlife, sheep, goats, chickens, stars & campfires.

Guest favourite
A rustic log cabin, dating back to the 1860s, is showcased with a front porch and a small decorative wreath on the door. The stone chimney stands tall beside the wooden structure, with a landscaped stone path leading up to the entrance.
Cabin in Georgetown
4.95 out of 5 average rating, 114 reviews

Griffith 1860 Log Cabin

Our 1860's log cabin is your perfect location. Close enough to tourist attractions and restaurants, yet away from traffic and distractions. Just 8 miles in the country from historic Georgetown, Kentucky, Kentucky Horse Park and Ark Encounter nearby. First floor bedroom has a queen bed with attached bath with tub and shower. Second floor bedroom with double bed, another second floor bedroom has 2 twin beds, sitting area day bed with trundle underneath. Bath with shower on second floor.

Top Guest favourite
An outdoor deck is visible, equipped with a round wooden table and four black chairs. The black exterior of the loft is complemented by large windows, allowing natural light to enter. Stairs lead down to a gravel path amidst greenery.
Farm stay in Stamping Ground
5 out of 5 average rating, 75 reviews

Modern Farm Loft

Welcome to our serene newly constructed Modern Farm Loft. Upstairs, our two-bedroom retreat offers views of our goat farm and tranquil countryside. Enjoy relaxing after exploring Keeneland horse racing, the Bourbon Trail, the Ark Encounter, and The Kentucky Horse Park. Cook with farm fresh duck eggs in the fully equipped kitchen. Interact with friendly farm animals or even lease our horse stalls if needed. Unwind on the private deck or by the fire under the starry skies. Book your stay today!

Top Guest favourite
A charming red cottage features a front porch with two rocking chairs and potted plants. The entrance is framed by two windows on either side of the door, providing a welcoming appearance. Tall trees and open space surround the property, enhancing the rural setting.
Cabin in Stamping Ground
4.97 out of 5 average rating, 39 reviews

Saddle’s & Boot’s

Woods and trails await you at our private country cottage! Imagine sitting by a bonfire and enjoying the country, shooting some hoops at the basketball goal or trying your hand at fishing in our stocked pond ! We have plenty of walking trails, or for the horse lovers we have three fenced pastures. All of this but only 5.5 miles from interstate 75 where you can do other activities such as the KENTUCKY HORSE PARK or THE ARK ENCOUNTER and so much more. Y’all hurry! So much to see in Kentucky

Top Guest favourite
Cabin in Georgetown
5 out of 5 average rating, 31 reviews

Overlook on the Elkhorn

Cozy cottage overlooking popular Elkhorn Creek! This vintage cottage is the perfect retreat for canoeing or just relaxing on the creek. Surrounded by horse farms, views front to back are serene. Large multi-level deck makes the perfect space to celebrate, grill out, and enjoy the surroundings. Direct creek access. Property also overlooks our brand new pickleball courts! Centrally located, just a few min to the adorable downtown Georgetown boutiques and restaurants. Perfect peaceful getaway!

Top Guest favourite
A red farmhouse tractor is positioned prominently in the foreground, with a vibrant red caboose labeled 'SOUTHERN X525' in the background. An outdoor pavilion with a gabled roof is partially visible, bordered by trees displaying autumn foliage.
Train in Lawrenceburg
4.99 out of 5 average rating, 552 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Top Guest favourite
Home in Stamping Ground
4.97 out of 5 average rating, 731 reviews

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

Top Guest favourite
An outdoor area features a gravel patio surrounded by lush greenery. Two wooden benches face a fire pit, with additional seating provided by tasteful Adirondack chairs. A shaded umbrella sits above a small table near the cabin entrance, creating a welcoming space for relaxation.
Cabin in Sadieville
4.97 out of 5 average rating, 320 reviews

*Unique Country Cabin *1BR 20 min from The Ark!

No neighbors! It’s not a big or fancy place but it’s clean, simple, and relaxing. The stars are brightest in the country when enjoying the fire pit. Our two story cabin has 1BR with two double beds, full kitchen, full bathroom, recliners, and grills. It's perfect for couples, friends, or small families. The Ark Encounter, Kentucky Horse Park, Keeneland, and several distilleries are all within an hour of the cabin. This is a great place to relax between visits to these attractions.

Top Guest favourite
Barn in Georgetown
4.99 out of 5 average rating, 91 reviews

New! Horse Farm stay! On Bourbon Trail!

The Loft at Pine Knoll Farm Kentucky is a unique horse farm stay located above our beautiful horse barn in the heart of horse country. We have prime views of the farm which is located in the center of the Bourbon Trail. 5 min to great restaurants in Midway! The Loft is 15 mins to The Kentucky Horse Park, 25 mins to Keenland, and Ark is 50 mins. Stabling/turnout available. We offer horse experiences/workshops/clinics through Kentucky Horse Experiences. Sign up to meet The Peace Ponies!

Guest favourite
Two outdoor bathtubs are positioned on a wooden deck, surrounded by trees and views of the creek. An Adirondack chair sits nearby, providing a space for relaxation while enjoying the natural surroundings.
Treehouse in Georgetown
4.93 out of 5 average rating, 315 reviews

KY’s #1 Wishlisted Stay-Treehouse and outdoor tubs

Escape to Kentucky’s 2026 most wishlisted Airbnb! A romantic treetop getaway with two outdoor tubs, twinkle lights, and a peaceful setting made for reconnecting. The treehouse features a large glass rolling garage door allowing stunning views of the sunset. The highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station ✔ Hot Water

Popular amenities for Stamping Ground holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Scott County
  5. Stamping Ground