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 spacious living area features warm wooden flooring and a traditional fireplace surrounded by a brick facade. Two armchairs are positioned near the fireplace, while a decorative cabinet adds character. Natural light filters through large windows, enhancing the welcoming ambiance.
Home in Perryville
4.97 out of 5 average rating, 73 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.

Superhost
Home in Harrodsburg
4.88 out of 5 average rating, 177 reviews

The Blue Cottage / Walk to Downtown Harrodsburg

Nestled amongst the site of Old Graham Springs is where you will find The Blue Cottage. Walking distance to Downtown Harrodsburg, this charming ranch home has been completely renovated & the owners spared no expense. Featuring 3 private bedrooms, 1 bath, hardwood floors, instgramable kitchen, and so much more! We are located 12 miles to Wilderness Trail Distillery, 1/2 mile to Haggin Hospital, 8 Miles to Shaker Village, and so much more. Enjoy staying in the oldest city West of the Appalachia

Top guest favourite
A ranch-style home is depicted with a light green exterior and dark shutters. A spacious covered front porch features two rocking chairs and a welcoming entryway, while neatly landscaped shrubs and grass surround the brick pathway leading to the front door.
Home in Danville
4.99 out of 5 average rating, 148 reviews

Walking distance to Centre, Main Street, hospital

Grant Place is a 2 bedroom, 2 full bathroom home located on a quiet street within walking distance to Centre College, Norton Center, Ephraim McDowell Hospital and Main Street. Located 4 miles to Wilderness Trail Distillery and 14 miles to Shaker Village. Grant Place is spacious and fully furnished with a well-stocked kitchen. The home features one king bed and one queen bed. We do provide a pack and play if you are traveling with a small child. Enjoy relaxing on our large covered front porch.

Top guest favourite
Home in Harrodsburg
4.94 out of 5 average rating, 207 reviews

The Betsy Sweat Cottage.

View the cottage on YouTube listed by the name of the cottage. Previous Guests have described the interior as (Quirky) …..compliment…August2026 UPDATES —- New flooring in bathroom and kitchen..New queen mattress and arrangement of furniture..This home is all Electric . Carbon Monoxide detector located beside bed .This is a Small Home. Close to Danville 9.5 miles (15 minutes away). , Frankfort 32 miles (40 minutes away). *** Notice. Neighborhood Highlights has Hosts Guidebook info .***

Top guest favourite
An outdoor gathering space is highlighted, featuring a circular structure with a metal façade. Strings of lights create a warm ambiance against the dusk sky. A large flat-screen television is mounted on the wall, complementing the open seating area with various tables and chairs.
Guest house in Springfield
4.99 out of 5 average rating, 138 reviews

Lofty Lodge on the Bourbon Trail

Come to the Bourbon Trail in the Heart of Kentucky! Stay at our beautiful lodge with large common areas perfect for hanging out! Our space is great for family trips, work retreats, or a couples get away! The lodge is located just 3 miles from from restaurants, groceries, pharmacies and shops. But at the Lodge you will enjoy the peace of the country. We are central to all the bourbon distilleries: 15mi to Maker's mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington and Louisville.

Top guest favourite
An elegant two-story white barn structure is set against a blue sky dotted with clouds. A prominent cupola with a weather vane crowns the roof. Trimmed bushes and small trees flank the sides, adding greenery to the scenic rural landscape.
Farm stay in Springfield
4.98 out of 5 average rating, 691 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 welcoming porch is displayed with an American flag hanging proudly. Green ferns and potted plants adorn the space, which is illuminated by string lights. The entrance features a dark door and a neatly painted white exterior, complemented by lush greenery surrounds.
Home in Danville
5.0 out of 5 average rating, 119 reviews

The Casa at Centre

This charming casa is conveniently located steps from the Centre football stadium and the Norton Center for Arts. It features 3 bedrooms and 2 bathrooms with 3 queen beds for 6 guests. Enjoy the outdoor space this place has to offer with an adorable front porch and a fully fenced in back yard with a firepit. Take a vibrant stroll to the heart of historically bold downtown Danville for an evening out of local eateries with a sweet Kentucky twist!

Top guest favourite
Home in Harrodsburg
4.97 out of 5 average rating, 107 reviews

The Robin's Nest

Welcome to the Robin's Nest, nestled in historical Harrodsburg, Kentucky! This recently remodeled 2-bedroom cottage is located in the heart of downtown, just steps away from boutiques, restaurants, bars and Old Town Park. Step inside The Robin's Nest and be greeted by a warm and inviting atmosphere. The living space is tastefully decorated creating a welcoming environment. Come celebrate the legacy of Harrodsburg the oldest city in Kentucky!

Guest favourite
The entrance to the 4th Street Retreat features a welcoming sign and a green door framed by beige siding. Natural light brightens the space, which is complemented by a small porch area. A colorful doormat adds a friendly touch to the entryway.
Flat in Danville
4.93 out of 5 average rating, 123 reviews

Welcome to 4th Street Retreat

A unique, peaceful, and spacious retreat to unwind and relax after a day visiting area sites or a night on the town. Spend time listening to vinyl records or watching a movie in the main living area, reading in the library, watching a throwback DVD or playing games in the loft, an intimate dinner in the dining room or kitchen, or watching the evening wind down from your own private deck.

Superhost
A spacious living area features a comfortable sofa and two armchairs arranged around a decorative coffee table. Large windows allow natural light to fill the room, while the newly refinished hardwood floors add a warm touch.
Home in Danville
4.8 out of 5 average rating, 173 reviews

Hometown Retreat

This single family home has been completely renovated with brand new appliances, newly refinished hardwood floors, remodeled bathrooms and more! It is fully furnished and within walking distance of Centre College and Downtown Danville. It is my pleasure to host you during your visit to the blue grass state! If you have any questions, please feel free to contact me directly.

Guest favourite
Home in Danville
5.0 out of 5 average rating, 18 reviews

Steps to Downtown Danville | Walk to Centre | 2BR

Welcome to a recently updated 2-bedroom, 1-bath stay in downtown Danville. This fun, stylish space blends modern and industrial design with florals and a touch of jungle. Located just behind Burke’s Bakery, you’re steps from shops, coffee, and events, and only a 5–10 minute walk to Centre College. Perfect for visiting students, local events, or a relaxed Bluegrass getaway.

Top guest favourite
A beautiful view of a sunset casts warm hues across the sky, illuminating a tranquil outdoor space. A fenced pool area is surrounded by lush greenery and colorful flowers, with a pathway leading to a charming barn and farmland beyond.
Flat in Harrodsburg
4.97 out of 5 average rating, 36 reviews

The Nook at Castaway Farm

Peaceful quaint horse farm surrounding a lovely retreat with country charm for relaxing around the pool or visiting horse farms, Keeneland or tasting at the nearby Bourbon Distilleries. Or bring your horses and stable them in the barn or field and enjoy riding at beautiful ShakerVillage, only 30 minutes away.

Popular amenities for Perryville holiday rentals