Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

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Top guest favorite

A well-maintained lawn features manicured grass and neatly arranged pathways leading to a circular seating area surrounded by lounge chairs. Lush greenery provides a natural backdrop, with serene views of the Ohio River visible beyond the landscaping.

Guest suite in Jeffersonville

4.94 out of 5 average rating, 205 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 private patio area is illuminated by string lights overhead, creating a cozy ambiance. Several seating options, including chairs and tables, are arranged among potted plants. The space is surrounded by greenery, enhancing the natural feel of the outdoor setting.

Guest suite in Prospect

4.86 out of 5 average rating, 189 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

The outdoor porch features a gray wooden deck with a dining table and four chairs, along with a bench. A welcoming door and a light fixture complete the entryway, adding charm to the cozy seating area.

Cottage in Prospect

4.98 out of 5 average rating, 119 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

An inviting outdoor space features a stone fire pit surrounded by several colorful seating options. Various patterned chairs and stools are arranged on a stone patio, with greenery providing a natural backdrop. A wooden table adds to the cozy ambiance of this fenced-in yard.

Guest suite in Louisville

4.94 out of 5 average rating, 278 reviews

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

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, 214 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 spacious home is visible, framed by greenery and a gravel pathway. Several outdoor chairs are arranged around a fire pit, while the deck features a covered seating area. The two-story structure showcases large glass windows, inviting natural light into the interior.

Home in Bedford

4.99 out of 5 average rating, 215 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

The image captures a street view of a charming downtown area, lined with brick buildings and shops. A modern vehicle is parked along the sidewalk, which is illuminated by natural light. Decorative string lights are visible overhead, enhancing the inviting ambiance of the setting.

Tiny home in La Grange

4.98 out of 5 average rating, 221 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

Home in La Grange

4.93 out of 5 average rating, 110 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

A well-defined pathway is illuminated by small lanterns, guiding guests toward the cottage nestled among trees. The gentle glow from the lights contrasts with the surrounding dusk, creating a serene approach to the inviting space.

Guesthouse in Shelbyville

4.97 out of 5 average rating, 112 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Top guest favorite

A clear window view showcases vibrant green trees outside, complemented by sunlight filtering through the leaves. A meandering stream can be seen in the distance, enhancing the natural beauty of the surrounding landscape.

Guest suite in Prospect

4.97 out of 5 average rating, 225 reviews

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

Top guest favorite

The interior of the geodesic dome features a welcoming entryway, with a dark door framed by large windows. Two stylish chairs are paired with a small table, and a kitchenette is visible, showcasing modern amenities. A scenic view of the countryside is unobstructed through the dome's curved window.

Dome in Mount Washington

4.98 out of 5 average rating, 170 reviews

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Top guest favorite

A young black lamb rests comfortably on a grassy patch, featuring a curly coat and distinctive white markings on its forehead. The background includes a softly blurred, woolly sheep, enhancing the calm farm environment.

Farm stay in Goshen

4.98 out of 5 average rating, 333 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....