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Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest suite in Jeffersonville

4.94 out of 5 average rating, 189 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.

Home in La Grange

5 out of 5 average rating, 229 reviews

Your Romantic Cabin with Hot tub

This cabin is a completely renovated 1940's farm house 10 minutes from historic downtown LaGrange. Guests have the entire home with front and back porch overlooking the big backyard. The master bedroom has a queen bed and the second bedroom has a full bed. The kitchen is fully equipped and ready for some country cooking. The fire pit is located in the back yard ready for you or you can use the gas fire pit just steps from the hot tub. The hot tub is ready for guests with a view of stars!

Cabin in Louisville

4.99 out of 5 average rating, 154 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.

Home in Louisville

4.98 out of 5 average rating, 106 reviews

Charming Bungalow on 1.5 Acres in Amazing Location

Peaceful. Private. Clean. Comfortable. Convenient. Hummingbird is a charming updated bungalow in one of Louisville's most coveted neighborhoods. Nestled on 1.5 acres of a historic street, you'll enjoy a park-like setting teeming with wildlife. Private, yet offering easy access to shopping, dining, entertainment, and major highways, and just 15 minutes from Valhalla Country Club, this hidden gem is sure to please. Whether here work, fun, or both, you’ll love your time at Hummingbird.

Cottage in Prospect

4.98 out of 5 average rating, 111 reviews

Cozy Cottage on Famous Kentucky Farm

A cozy cottage house on Foxhollow Farm, featured on Season 16 of Bravo's Top Chef, a grassfed beef farm just 20 minutes from downtown Louisville. Enjoy the serene landscape of a 1,300-acre family farm during your stay in The Fox Den Cottage, surrounded by horses, cattle set to pasture, and the natural sounds of chickens and roosters. Just 25 minutes from Churchill Downs, it's perfect for Oaks/Derby or a relaxing visit to the Bluegrass State to enjoy Louisville’s treasures, like bourbon.

Tiny home in La Grange

4.98 out of 5 average rating, 194 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 suite in Louisville

4.95 out of 5 average rating, 152 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!

Guesthouse in Shelbyville

4.97 out of 5 average rating, 101 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.

Guest suite in Prospect

4.97 out of 5 average rating, 203 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.

Home in Simpsonville

4.98 out of 5 average rating, 612 reviews

Private Lower Level King Bed/Patio

Guests access to the private finished walkout basement, fully fenced back yard. Near Bluegrass Outlet Mall & Louisville. An hour to Cincinnati & 45 to Lexington. King in the first bedroom, queen in second, sectional w/ reclining seats. Private patio/entry. Farm view, shopping, restaurants. Smoke-free! Homeowners live upstairs. Must be able to use stairs or walk a slight incline on the side yard. Cable offered on Smart TVs. Apps accessible. Fire pits.

Farm stay in Goshen

4.98 out of 5 average rating, 316 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....

Home in Pewee Valley

4.97 out of 5 average rating, 150 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!

Vacation rentals for every style

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Popular amenities for Crestwood vacation rentals

Free parking on premises

Air conditioning

Stay near Crestwood's top sights

Yew Dell Botanical Gardens22 locals recommend

Kentucky Artisan Distillery12 locals recommend

3rd Turn Oldham Gardens10 locals recommend

Rikishi4 locals recommend

The Maples Park4 locals recommend

Jucy's Smokehouse Bar-B-Q4 locals recommend

Other great vacation rentals in Crestwood

Condo in La Grange

4.98 out of 5 average rating, 66 reviews

The Beje (‘bay-hay’)-King Bed-Coffee Bar

Farm stay in Simpsonville

5 out of 5 average rating, 21 reviews

Horse Farm 4Bedrm home Bourbon Trail ~private pool

Rental unit in Prospect

4.82 out of 5 average rating, 33 reviews

Stay In Smithsonian's of American Gardens Collect.

Home in Crestwood

4.92 out of 5 average rating, 84 reviews

12 Guest/Top Area /Families/Park

Home in Jeffersonville

4.99 out of 5 average rating, 67 reviews

Beachfront River Cottage

Guest suite in Louisville

4.9 out of 5 average rating, 49 reviews

Spacious one bedroom first floor suite

Home in Crestwood

4.95 out of 5 average rating, 21 reviews

The Yellow House @ Floydsburg

Home in La Grange

4.91 out of 5 average rating, 74 reviews

Caboose Cottage

Quick stats about vacation rentals in Crestwood

Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
260 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Frequently Asked Questions

What are the most popular amenities for House Rentals in Crestwood?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Crestwood?
Experience the best of Crestwood with our house rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Crestwood have wireless internet?
Absolutely! We offer over 10 house rentals with wireless internet in Crestwood. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Crestwood?
Crestwood has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Crestwood have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Crestwood. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Crestwood?
Yes! Work meets play with ease at over 10 vacation rentals in Crestwood featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore