Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

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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, 117 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.

Guest favorite

Farm stay in Crestwood

4.97 out of 5 average rating, 35 reviews

Maple's Place - *charm*country*hot tub*bourbontour

Maples Place Built in 1890 and meticulously remodeled down to the studs, Maple's Place combines historic charm with modern amenities. The house has all-new HVAC, electrical, plumbing, roofing, and siding. The home features three beautifully decorated bedrooms, two full bathrooms, and one half-bath. The master bath is a haven of luxury with a walk-in shower and a soaking tub. Each room is thoughtfully designed. Outside, enjoy a spacious deck and pergola, complete with an 8-person hot tub.

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, 209 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

An open-concept living area features a cozy sofa and armchair, with light-colored walls and wooden beams above. The modern kitchen, equipped with stainless steel appliances and a spacious island, is complemented by bar seating and a view of the outdoors through a window.

Home in Crestwood

5 out of 5 average rating, 54 reviews

Briar Creek Cottage

Welcome to this cozy 2-bed, 2-bath cottage, just 25 minutes from the Louisville Airport & conveniently close to the Kentucky Bourbon Trail. Recently renovated, this cottage is nestled in a peacefully wooded lot with modern amenities. The primary suite includes a queen bed, an en suite bathroom, and an optional pack-n-play. The second bedroom also features a queen bed and adjacent bath. Perfect for a tranquil getaway or exploring the Kentucky Bourbon Trail. Book now for a charming retreat!

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, 216 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, 108 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, 111 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, 223 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

A geodesic dome is positioned on a gravel road, surrounded by trees. A covered seating area is visible nearby, with chairs arranged to view the expansive countryside. The sunrise paints the sky in soft hues of orange and pink, creating a serene backdrop over a misty landscape.

Dome in Mount Washington

4.98 out of 5 average rating, 163 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

Farm stay in Goshen

4.98 out of 5 average rating, 331 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, 162 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!

Top guest favorite

Several chickens roam freely in a green pasture area, surrounded by a wooden fence. A gated enclosure is visible in the background, with trees lining the perimeter, adding a natural setting to the farm landscape.

Farm stay in La Grange

4.95 out of 5 average rating, 709 reviews

The Cottage at StoneLedge 2 bedroom/1bath

Nestled on an expansive 80 acre horse farm, the cottage is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. If traveling with pets please note prior approval is required and be sure to read the pet policy in 'other things to note'. Thank you for your consideration.

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Popular amenities for Crestwood vacation rentals

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Other great vacation rentals in Crestwood

Guest favorite

A cozy seating area is presented with two red armchairs positioned beside a small green table. Above the table, a floral artwork adds a touch of color to the wall. A flat-screen television is mounted, and natural light enters through a large window covered by a dark curtain.

Condo in Jeffersonville

4.92 out of 5 average rating, 145 reviews

Cozy penthouse with entertainment and food nearby

ChristinaRating, 5 stars3 days ago

Beautiful space and location! We just needed a place to stay on the way to Mammoth CaveNP but made us consider coming back to Jeffersonville in the future!

Top guest favorite

The cabin sign, illuminated softly at night, features a rustic wooden background with a metal cutout displaying the words 'Bourbon Country Cabins' alongside a silhouette of a tree and a cabin. The subtle lighting adds clarity to the detailed craftsmanship.

Cabin in Mount Eden

4.98 out of 5 average rating, 146 reviews

Bourbon Country Cottage

AndrewRating, 5 stars2 weeks ago

We had a fantastic stay at this property! Beautiful and quiet area and the property had everything we needed. Close to many distilleries and horse farms. We will definitely be back again.

Guest favorite

A clear swimming pool is surrounded by a smooth concrete deck and a white picket fence. Lush greenery and trees are visible in the background, reflecting gently on the water's surface.

Cottage in Taylorsville

4.89 out of 5 average rating, 123 reviews

Best view of the lake two bed two bath cottage #4

WilliamRating, 5 stars1 week ago

The cottage was very accommodating and very clean. It had everything we needed for our stay. Check in and check out was very easy. The host was amazing and very helpful. We would definitely recommend to others.

Guest favorite

A spacious outdoor pool area features a large swimming pool surrounded by lounge chairs. A hot tub is positioned at one end, while greenery lines the perimeter, providing a tranquil atmosphere. The surrounding building and pathway enhance accessibility for guests.

Apartment in Central Business District

4.99 out of 5 average rating, 108 reviews

Sleek Luxury Apt: King Bed, Coffee Bar & Pool!

JacobRating, 5 stars2 weeks ago

Beautiful place to stay! The host’s were very quick to respond with any issues and had many great recommendations. Well worth the money!

Guest favorite

Cottage in Spencer County

4.91 out of 5 average rating, 151 reviews

Peaceful Cottage Minutes from Lake Access

JamesRating, 5 stars2 months ago

We enjoyed our stay very much. Home was exactly what we were looking for with our selection. Peaceful area with hiking near the home in the Taylorsville State Park.

Guest favorite

A welcoming entrance is highlighted by a set of stone steps leading to a covered porch. Vibrant flowers enhance the greenery, while elegant architectural details are seen on the house. The porch features a decorative railing and a couple of seating areas for relaxation.

Apartment in Louisville

4.83 out of 5 average rating, 129 reviews

Highlands Harmony House - Near Cherokee Park

KaylaRating, 5 stars1 month ago

Thank you for allowing us to share your space for a few nights!

Superhost

The entrance to Edgewater Resort is marked by a stone sign featuring the name in green lettering. Surrounding the sign are trees and well-maintained landscaping, providing a welcoming indication of the nearby cottages and amenities.

Cottage in Taylorsville

4.71 out of 5 average rating, 166 reviews

Get Away From It All

WhitneyRating, 5 stars2 months ago

We had a wonderful time staying at Jared’s cottage! Felt right at home! There was an issue with the hot tub but he had someone come out right then and there to take care of the issue. Very responsive and flexible!

Guest favorite

Condo in Original Highlands

4.93 out of 5 average rating, 197 reviews

Large Townhouse, Walk to All! King beds, 2.5 baths

ChrisRating, 5 stars1 month ago

We really enjoyed our stay! It was exactly as pictured and described. The space was very clean. Deirdre was very prompt with communication and polite. We would highly recommend!

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Vacation rentals in Crestwood

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