Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

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Top guest favorite

An outdoor fire pit is surrounded by several wooden chairs, providing a gathering space for relaxation. The calm waters of the Ohio River reflect the night sky, with soft lights from boats creating a serene atmosphere. Low greenery and gentle clouds frame the scene.

Guest suite in Jeffersonville

4.94 out of 5 average rating, 217 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Guest favorite

A cozy seating area is surrounded by large windows, allowing natural light to fill the space. Two armchairs with dark upholstery face a decorative white coffee table, which is centered on a textured area rug. A bench with cushions adds to the inviting atmosphere.

Guest suite in Prospect

4.86 out of 5 average rating, 190 reviews

Private Entry, full suite w/game rm. Kitchenette.

Golf course community, walkout basement with private entry. Flat screen TV, WiFi, Private Bedroom. Large Family rm with pull out Queen sleeper sofa, pool table, Hardwood floors. Refrigerator, microwave and coffee maker, Keurig. Toaster/hot plate and basic dishes/ cooking utensils are included. (one review stated dishes weren't clean) I was trying the whole open shelf look and didn't realize I would need to clean the dishes more often since they weren't in a cabinet) Private patio. Large yard.

Top guest favorite

A cottage is nestled among lush greenery, featuring a well-maintained lawn and vibrant flower beds. The exterior includes classic shutters and a prominent stone chimney, surrounded by mature trees that provide ample shade.

Cottage in Prospect

4.98 out of 5 average rating, 122 reviews

Cozy Cottage on Famous Kentucky Farm

Experience the beauty of Kentucky farmland with hundreds of acres to explore, including our nature trail where you might spot our beef cattle and horses. Relax on the charming front porch, watch the fireflies, and soak in the peaceful atmosphere. Our cottage features a homey and cozy feeling with two spacious bedrooms: a master bedroom with a comfortable queen bed and a second bedroom with a full-size bed, perfect for families or couples. Perfect to explore the events like the Kentucky Derby.

Top guest favorite

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

5 out of 5 average rating, 235 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Top guest favorite

A light-filled dining area features a wooden table surrounded by white chairs. A blue area rug anchors the space, complemented by a chandelier above. A kitchen bar with seating is visible in the background, and large windows provide views of the surrounding trees.

Home in Bedford

4.99 out of 5 average rating, 218 reviews

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 160 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

Top guest favorite

A spacious studio-style room features a four-poster bed with white bedding. A comfortable armchair sits nearby, and a flat-screen TV is positioned on a wooden entertainment unit. Natural light enters through patterned curtains, illuminating the warm wood flooring.

Tiny home in La Grange

4.98 out of 5 average rating, 230 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Guest favorite

A cozy living area features a light grey sectional sofa accompanied by an accent chair adorned with orange cushions. Framed art pieces hang on a teal wall, while a wood coffee table sits atop a patterned rug. Natural light enters through a window covered with sheer curtains.

Guest suite in Louisville

4.95 out of 5 average rating, 158 reviews

Derby City Hideaway

Whiskey Hollow offers you a unique stay with our Bourbon-themed space. Your stay in Kentucky is sure to be memorable and cozy. Our guest suite offers a full kitchen, cozy living area, bedroom and full bath with a private patio. Local attractions include Churchill Downs, home of the Kentucky Derby, Kentucky Derby Museum. Louisville Slugger Museum, Kentucky Bourbon Trail, local city eats, 4th Street Live, horse farms, hiking, waterfalls, parks, shopping, local arts, and much more!

Superhost

The image shows a hot tub on a covered deck, with bubbling water and a view of a backyard fire pit area below. Four blue Adirondack chairs surround the fire pit, which is under a canopy of string lights amidst lush greenery.

Home in La Grange

4.9 out of 5 average rating, 114 reviews

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

Guest favorite

The living area features a spacious sectional sofa arranged around a round wooden coffee table. Natural light filters through sheer curtains, illuminating the room. Decorative shelves are mounted on the walls, and a ceiling fan is present for comfort.

Home in Crestwood

4.91 out of 5 average rating, 112 reviews

12 Guest/Top Area /Families/Park

Welcome to our Family Airbnb 1- Great Location in residential neighborhood 2- 20 Min to Kentucky Derby Museum 3 - 20 Min to Louisville Mega Caverns 4- 15 Min Evan William Bourbon 5- 20 Min Churchill Down 6- Designed for 2 guests (3 Queen Bed, 1 double Bunk bed, 1 Queen Air Mattress) 7- Free Parking (2 Cars Inside and 2 Cars Outside) 8- Fully Equipped Kitchen 9- Fast Wi-Fi 10- Quiet and Safe Area 11- Private Patio 12-24/7 Available Host 13- 2 Smart TVs 14- Laundry In Unit

Top guest favorite

The bedroom features a spacious king-sized bed, adorned with decorative pillows, and a stylish ceiling fan above. A wooden chest sits at the foot of the bed, complemented by a desk and chair in the corner. Natural light enters through window treatments, illuminating the room.

Guesthouse in Louisville

4.97 out of 5 average rating, 132 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

Top guest favorite

The exterior of a renovated farmhouse is surrounded by lush greenery. A spacious porch with seating is visible at the front, while a gravel path leads to the inviting entrance. The structure features a metal roof and warm-colored trim that complements the natural setting.

Farm stay in Goshen

4.98 out of 5 average rating, 344 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

Top guest favorite

An outdoor fire pit area is surrounded by Adirondack chairs arranged in a circular pattern. Warm string lights hang overhead, illuminating the space, while the house stands in the background against a vibrant sunset sky.

Home in Pewee Valley

4.98 out of 5 average rating, 168 reviews

Bourbon Trail*Pewee Valley *HOT TUB

Welcome to the Bourbon Bungalow, a tastefully restored farmhouse on the famous Kentucky Bourbon Trail. This southern retreat is on the outskirts of Louisville in the quaint city of Pewee Valley. A short drive to some of the states most sought after locations such as Churchill Downs, bourbon distilleries, horse parks, caves, Shelbyville, Bardstown, & more! The Bourbon trail is waiting for you!