Holiday rentals in Perryville

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Top-rated holiday rentals in Perryville

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, 235 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
Home in Springfield
4.99 out of 5 average rating, 102 reviews

Bourbon Trail + Events + Hot Tub +Walk 2 Dine

Charming, spotless, and historic yet modern, a few words from 5-star reviews! The Kentucky Barrel House a unique retreat on the Bourbon Trail. Take a dip in the hot tub- grab a towel from the warmer, chat by the firepit. Pet-friendly, fenced yard. Equipped kitchen, or walk to downtown restaurants. Minutes to: Maker’s Mark, Willett, Bardstown Bourbon, Heaven Hill, Beam and many more. Near Cornerstone Acres Events, The Grove At Silverton Hill, My Old Kentucky Home. Celebrate National Bourbon Week!

Top guest favourite
Home in Perryville
4.97 out of 5 average rating, 65 reviews

Historical Haven

Historical Haven is a unique cottage that will not disappoint. This renovated circa 1840 Dry Goods store is located on Merchants Row. Take a step back in time as you visit one of the only intact 19th-century mercantile districts in the nation. Enjoy a historical walking tour and do some shopping as you take in the scenery. With riverside views and a large deck it’s an ideal place to stay for a Bourbon Trail excursion, visiting Centre College, enjoying area attractions, or just relax and unwind.

Guest favourite
The image collage features various spaces of a stylish home. A cozy lounge area with a fireplace is shown, alongside an outdoor hot tub surrounded by greenery. The dining area is connected to a deck, and a game room with a bar creates an inviting entertainment space.
Home in Bardstown
4.96 out of 5 average rating, 119 reviews

StillHill: HotTub GameRoom Whiskey Lounge Acreage

Stylish 3 bedroom home located in the Bourbon Capital is a perfect getaway to be still or tour the best Kentucky bourbon from a local whiskey still. Centrally located within 25 miles of 10 distilleries! Close to the Old Kentucky dinner train, the Derby, and a short drive to Louisville & Lexington. Enjoy 5 private acres where you can soak in the hot tub, swing on the patio, sit by the fire and watch the birds and deer. Then relax in our indoor lounge or garage game room after a day of adventures

Guest favourite
The exterior of a charming red barn is shown, featuring white accents and a welcoming front door. A wreath adorns the door, and colorful autumn decorations are placed at the base, complemented by lush greenery and a peaceful sunset backdrop.
Barn in Harrodsburg
4.87 out of 5 average rating, 248 reviews

The Beaumont Parlor, 8 miles to Shaker Village

It's rare to find a place that's both historic & one-of-a-kind. That's exactly what you are going to get at The Beaumont Parlor! Formerly an old milk barn & milk parlor for the City of Harrodsburg, this newly restored unit features old world charm & all the modern amenities a guest could ask for. Featuring a King bed, Queen Sleeper Sofa & Full Bathroom. The Owner's have spared no expense and you will find charm at every angle. Guests will be able to walk to Beaumont Inn & Downtown Harrodsburg

Top guest favourite
The cottage features a charming exterior with light pink siding and a newly landscaped front yard. A pair of wooden chairs is positioned on the porch, surrounded by blooming flowers and freshly mulched areas, creating a welcoming approach.
Cottage in Danville
5 out of 5 average rating, 217 reviews

Quaint cottage in the heart of Danville

Cute renovated cottage in the heart of historic Danville. Walking distance to downtown and all of Centre College. Enjoy local restaurants, the Saturday morning Farmers Market, and the amazing shops on Main Street. The Cottage is fully furnished and beautifully decorated to make your stay comfortable and relaxing. All beds are memory foam mattresses, and all linens are 100% cotton with hypoallergenic fiber filled pillows and comforters. The front porch & deck offer outdoor space to sit a while!

Top guest favourite
Farm stay in Springfield
4.98 out of 5 average rating, 682 reviews

The Getaway in Bourbon Country with Breakfast

Located in the heart of the Bourbon Trail. Come and enjoy the peace and quiet of country living, but still close enough to cities. When you first arrive, you will find the entrance on a large, covered patio. There is a gas grill there for your use. We also have a fire pit, so bring wood. Feel free to take a walk down to the river at the bottom of our property. There you will find a park like setting where you can relax and listen to nature if you like. Eggs, bacon and biscuits provided.

Top guest favourite
A porch area is featured, with a wooden swing and two rocking chairs positioned around a fire pit. Lush greenery surrounds the space, and the calm river is visible just beyond the grass, framed by trees on either side.
Cabin in Wilmore
4.95 out of 5 average rating, 165 reviews

Highbridge River Cabin, Private Dock, EV Charger

Relax at the river cabin. Retreat right on the Kentucky River with private dock for easy river access. The cabin has Dual Plug Type 2 EV charger. Cozy cabin on stilts with stone fireplace & porch with table and chairs. Surrounded by nature & beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 mins or less from LEX Airport, Keeneland and Shaker Village. No extra guests without permission, no parties.

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, 541 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
A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.
Home in Versailles
4.95 out of 5 average rating, 238 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

Top guest favourite
A wooden cabin is set against a backdrop of greenery, featuring a spacious wrap-around porch. Sturdy wooden steps lead to the entrance, and large windows provide natural light. The surrounding area is lined with trees, offering a serene and private outdoor setting.
Cabin in Springfield
4.93 out of 5 average rating, 255 reviews

Cozy Cabin on the Bourbon Trail

Our place is close to the Bourbon Trail. You’ll love our cabin because of the warm interior and amazing outdoor space. Our place is good for couples, solo adventurers, business travelers, and families. This cabin located in the country on our 100 acre farm, but you are 3 miles from restaurants, groceries, pharmacies and shops. The location is also central to the distilleries: 15mi to Maker's Mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington, and Louisville

Guest favourite
A modern A-frame cabin is depicted, showcasing a welcoming porch with two wooden chairs. The structure features a dark exterior complemented by large windows and a distinctive peaked roof. The front door, painted in a soft orange hue, adds a pop of color to the facade.
Villa in Harrodsburg
4.91 out of 5 average rating, 107 reviews

Bourbon Villa at Daynabrook Farm, Hot Tub-3

Keep it simple and escape to the rolling bluegrass hills and experience the magic of Kentucky's Bourbon Trail with an unforgettable stay at Daynabrook Farms. A full kitchen makes for effortless in-cabin dining, Private hot tub, scenic views of the countryside from your private back porch, convenient location to Lexington (20 min. to Airport), Louisville, Frankfort, and Danville. Areas around Hot tub, pools, and shower are wet, please exercise caution when in use.

Popular amenities for Perryville holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Boyle County
  5. Perryville