Crestwood Vacation Rentals

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Our top choices for Crestwood vacation rentals

Hancock House

Hancock House
3.0 star property
Downtown Louisville
8.2 out of 10, Very good, (248 reviews)
"Great stay!"
United States
Tim
Hancock House

Stellar Suites

Stellar Suites
4.5 star property
Downtown Louisville
9.6 out of 10, Exceptional, (119 reviews)
"The check-in process was simple and easy, the room was spotless and had so many amenities. "
United States
Grace
The price is CA $157
CA $254 total
includes taxes & fees
Mar 11 - Mar 12
Stellar Suites

CozySuites at Nulu

CozySuites at Nulu
4.0 star property
Downtown Louisville
8.0 out of 10, Very good, (27 reviews)
"The unit was clean, all communications were timely, the property has all the amenities, and NULU is very walkable. A perfect stay! My only regret is that I wasn't able to extend the stay. Highly recommended if you're in the Louisville area "
United States
William
The price is CA $90
CA $263 total
includes taxes & fees
Mar 9 - Mar 10
CozySuites at Nulu

New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
South Louisville
10.0 out of 10, Exceptional, (23 reviews)
"Very clean place, easy check in, Felix was very nice and super responsive "
United States
Will J.
The price is CA $48
CA $230 total
includes taxes & fees
Feb 10 - Feb 11
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Clifton
10.0 out of 10, Exceptional, (31 reviews)
"Our stay was very pleasant, great location, lots of great restaurants. Tyler the host was was always available when we had an issue. "
United States
Max D.
The price is CA $68
CA $229 total
includes taxes & fees
Feb 16 - Feb 17
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Stylish House Walking Distance from the Fun of the Highlands!

Stylish House Walking Distance from the Fun of the Highlands!
Phoenix Hill
9.6 out of 10, Exceptional, (24 reviews)
"We will stay here over and over again. It’s a lovely place that a perfect location."
United States
Jennifer H.
The price is CA $62
CA $230 total
includes taxes & fees
Feb 9 - Feb 10
Stylish House Walking Distance from the Fun of the Highlands!

The Reserve on Main

The Reserve on Main
4.0 star property
Downtown Louisville
10.0 out of 10, Exceptional, (1 review)
"Incredible stay. This stay was clean and inspiring for anyone wishing to take a break and recharge. We highly recommend this stay to everyone staying in the city. "
Canada
georgios
The price is CA $226
CA $330 total
includes taxes & fees
Feb 9 - Feb 10
The Reserve on Main

The Duke Hotel

The Duke Hotel
2.0 star property
Downtown Louisville
The price is CA $88
CA $181 total
includes taxes & fees
Feb 9 - Feb 10
The Duke Hotel

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
10.0 out of 10, Exceptional, (19 reviews)
"Awesome place, it was clean and spacious! "
United States
Ben M.
The price is CA $199
CA $611 total
includes taxes & fees
Feb 9 - Feb 10
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!

Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
Jeffersonville
9.8 out of 10, Exceptional, (30 reviews)
"Perfect place to stay. Close to town with a lot to do. Nice quiet area. "
United States
Dakota H.
The price is CA $62
CA $178 total
includes taxes & fees
Feb 16 - Feb 17
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!

4th Street Suites - Extravagant King Bed Suite

4th Street Suites - Extravagant King Bed Suite
Downtown Louisville
9.8 out of 10, Exceptional, (22 reviews)
"Clean room and great location. Enjoyed being able to walk to many restaurants and to tours. "
United States
Doug H.
The price is CA $65
CA $208 total
includes taxes & fees
Feb 9 - Feb 10
4th Street Suites - Extravagant King Bed Suite

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
8.8 out of 10, Excellent, (37 reviews)
"Clean room, history and location. "
United States
RICHARD
The price is CA $167
CA $194 total
includes taxes & fees
Feb 9 - Feb 10
The Bellwether Hotel

Luxurious Spacious Apartment in the Heart of Downtown! King Bed, Gym, Pool!

Luxurious Spacious Apartment in the Heart of Downtown! King Bed, Gym, Pool!
Downtown Louisville
9.8 out of 10, Exceptional, (14 reviews)
"Great stay. Tyler was an excellent host as was the property. Will be our go to place next time in Louisville. "
United States
Carol G.
The price is CA $68
CA $206 total
includes taxes & fees
Feb 16 - Feb 17
Luxurious Spacious Apartment in the Heart of Downtown! King Bed, Gym, Pool!

Germantown Fav! BOOK for MATS, DERBY 2026!

Germantown Fav! BOOK for MATS, DERBY 2026!
Germantown
10.0 out of 10, Exceptional, (72 reviews)
"Cute comfortable house would go again"
United States
Hope N.
The price is CA $93
CA $251 total
includes taxes & fees
Feb 9 - Feb 10
Germantown Fav! BOOK for MATS, DERBY 2026!

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.6 out of 10, Excellent, (10 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is CA $64
CA $185 total
includes taxes & fees
Feb 10 - Feb 11
Alfesco - Walkable Highlands Guesthouse

King Bed in Historic Building Downtown

King Bed in Historic Building Downtown
Downtown Louisville
9.2 out of 10, Wonderful, (39 reviews)
" Nice stay in a fun city!"
United States
Jennifer S.
The price is CA $72
CA $194 total
includes taxes & fees
Feb 9 - Feb 10
King Bed in Historic Building Downtown

Lavish Apartment in the Heart of Downtown! Pool, Gym, King Bed, Coffee Bar!

Lavish Apartment in the Heart of Downtown! Pool, Gym, King Bed, Coffee Bar!
Downtown Louisville
10.0 out of 10, Exceptional, (43 reviews)
"Great location!"
United States
Michelle H.
The price is CA $75
CA $213 total
includes taxes & fees
Feb 16 - Feb 17
Lavish Apartment in the Heart of Downtown! Pool, Gym, King Bed, Coffee Bar!

Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun

Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun
Shelbyville
9.8 out of 10, Exceptional, (19 reviews)
"Great location, responsive hosts, fantastic property!"
United States
Timothy S.
The price is CA $323
CA $712 total
includes taxes & fees
Feb 9 - Feb 10
Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Crestwood Hotel Reviews

Find out more about Crestwood

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Crestwood. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Crestwood?

Yes, we offer vacation rentals in Crestwood near Yew Dell Botanical Gardens, or you can select a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Crestwood has to offer?

Charming home in the heart of the city!: Visitors like this Crestwood vacation home rental. It is equipped with a selection of games, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Crestwood?

Expedia has 7 vacation rentals for your stay in Crestwood.

What’s there to see and do in Crestwood?

Yew Dell Botanical Gardens and Summer Field by the Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Open Range Sports. Other places in town to visit include South Oldham Library and Kentucky Artisan Distillery.

What’s a vacation rental in Crestwood like?

Vacation rentals are private properties you can book for a long or short time in Crestwood. Vacation rentals feature extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.