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Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

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Guest suite in Jeffersonville

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.

Cottage in Prospect

Cozy Cottage on Famous Kentucky Farm

A cozy cottage house located on Foxhollow Farm, featured on Season 16 of Bravo's Top Chef, a grassfed beef farm located 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 and cattle set to pasture. Located just 25-minutes from Churchill Downs, this cottage is ideal for your Oaks/Derby stay, or a casual, relaxing visit to the Bluegrass State to enjoy Louisville's many treasures like bourbon.

Guest suite in Louisville

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.

Home in Bedford

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.

Guest suite in Louisville

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 newly renovated space 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!

Tiny home in La Grange

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 Prospect

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.

Guesthouse in Louisville

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.)

Cottage in Pleasureville

The Cozy Cottage on One Goat Farm

This quaint little cottage is located on the Bourbon Trail of Kentucky. A mere 9 minutes from Six-Mile Distillery, it is also in close proximity to a gas station, grocery and library. Located in the heart of an Amish community, you will hear horses and buggies clip-clopping past as you sip your morning coffee. This cottage is on a functioning farm with horses, cats, goats and donkeys, with overnight housing facilities for your own equines as well.

Home in Louisville

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

Farm stay in Goshen

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

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

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Crestwood vacation rentals

Free parking on premises

Air conditioning

Stay near Crestwood's top sights

Yew Dell Botanical Gardens22 locals recommend

The Maples Park4 locals recommend

Jucy's Smokehouse Bar-B-Q4 locals recommend

Other great vacation rentals in Crestwood

Cabin in Salem

Dee's Country Cabin

Guest suite in Crestwood

Charming suite in Bourbon Country

Guesthouse in Prospect

Prospect Guest House

Rental unit in Pewee Valley

Loft in Pewee Valley

Guest suite in Louisville

Spacious one bedroom first floor suite

Guest suite in Shelbyville

Spacious suite, country views, pool table, firepit

Condo in La Grange

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

Loft in La Grange

Lagrange Loft - Small Town USA - Bourbon Trail

Quick stats about vacation rentals in Crestwood

Total rentals
20 properties
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Wifi availability
20 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
200 reviews
Nightly prices starting at
$50 before taxes and fees

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 $140 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 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore