Crestwood Vacation Rentals

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Our top choices for Crestwood vacation rentals

Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (31 reviews)
"The VRBO was perfect. Has the elegant modern feel just like the pictures show and has lots of space to hang out and relax. Loved the location and how walkable it was to coffee shops, restaurants, and bars. Loved staying here and highly recommend!"
United States
Lucas L.
The price is CA $139
CA $264 total
includes taxes & fees
May 26 - May 27
Unique Downtown Studio with an Industrial Vibe

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville
10.0 out of 10, Exceptional, (19 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
The price is CA $131
CA $252 total
includes taxes & fees
May 24 - May 25
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
The price is CA $173
CA $479 total
includes taxes & fees
May 24 - May 25
Quiet Downtown Maple Cottage Gem

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
9.8 out of 10, Exceptional, (34 reviews)
"Very convenient stay. Easily fit the needs to access area we needed to stay in and place was comfortable clean."
United States
Michelle W.
The price is CA $56
CA $240 total
includes taxes & fees
May 27 - May 28
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (10 reviews)
"It was everything we needed."
United States
Carmen C.
The price is CA $105
CA $550 total
includes taxes & fees
May 31 - Jun 1
St. Matthew’s - Walk to Shops & Restaurants

Whiskey Stop-Close to Ky Expo, Walkable & Parking!

Whiskey Stop-Close to Ky Expo, Walkable & Parking!
Germantown
10.0 out of 10, Exceptional, (76 reviews)
"The amenities were great and the house was the perfect spot for our weekend getaway. "
United States
Janessa D.
The price is CA $118
CA $272 total
includes taxes & fees
Jun 15 - Jun 16
Whiskey Stop-Close to Ky Expo, Walkable & Parking!

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
New Albany
10.0 out of 10, Exceptional, (45 reviews)
"Clean great location and host "
United States
Donna L.
The price is CA $95
CA $272 total
includes taxes & fees
Jun 10 - Jun 11
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

A Derby getaway – only minutes to Churchill Downs!

A Derby getaway – only minutes to Churchill Downs!
Paristown Pointe
10.0 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Nakoma F.
The price is CA $118
CA $319 total
includes taxes & fees
May 21 - May 22
A Derby getaway – only minutes to Churchill Downs!

King Bed in Historic Building Downtown

King Bed in Historic Building Downtown
Downtown Louisville
9.2 out of 10, Wonderful, (42 reviews)
"This place was well worth the stay and the host was very accommodating"
United States
Roger C.
The price is CA $74
CA $197 total
includes taxes & fees
May 25 - May 26
King Bed in Historic Building Downtown

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (19 reviews)
"House was cozy, and host was responsive. Rooms were clean and welcoming. A lovely place to stay."
United States
Alec S.
The price is CA $148
CA $222 total
includes taxes & fees
Jun 2 - Jun 3
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Louisville
9.8 out of 10, Exceptional, (147 reviews)
"Very nice couple , will stay there again"
United States
Bryan S.
The price is CA $350
CA $557 total
includes taxes & fees
May 25 - May 26
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (39 reviews)
"This is a great little place to stay! Close to the Exposition Center and a lot of other attractions. It is an older place but clean and comfortable. This is our second stay at this place. "
United States
jaggers959
The price is CA $144
CA $375 total
includes taxes & fees
May 25 - May 26
Close to Everything in Louisville!!!

Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Louisville
10.0 out of 10, Exceptional, (20 reviews)
"Everything was outstanding!"
United States
John W.
The price is CA $245
CA $389 total
includes taxes & fees
May 25 - May 26
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

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, (33 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 $96
CA $265 total
includes taxes & fees
May 25 - May 26
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

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, (54 reviews)
"What a amazing stay! The description for this apartment doesn't do it justice! The pool, hot tub, coffee bar, golf simulator, pool table and lounge are some of the amenities you receive with this amazing property. The location was great as well! Just blocks away from 4th Street Live and many other downtown attractions. Book your stay here and you will not be disappointed!!"
United States
Aaron
The price is CA $103
CA $246 total
includes taxes & fees
May 21 - May 22
Lavish Apartment in the Heart of Downtown! Pool, Gym, King Bed, Coffee Bar!

Uptown Class

Uptown Class
New Albany
10.0 out of 10, Exceptional, (21 reviews)
"Great house plenty of room for our group of 12 quiet street but close to alot to do"
United States
Brandon P.
The price is CA $172
CA $575 total
includes taxes & fees
May 21 - May 22
Uptown Class

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Shelby Park
9.6 out of 10, Exceptional, (23 reviews)
"This home is warm and cozy and close to everything we had planned."
United States
Dawn G.
The price is CA $130
CA $315 total
includes taxes & fees
May 24 - May 25
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

Theatre District Condo | Gym • Free Parking • DT

Theatre District Condo | Gym • Free Parking • DT
Downtown Louisville
9.6 out of 10, Exceptional, (24 reviews)
"Absolutely amazing stay here! It was super clean, comfortable and the perfect location for a concert at The Palace! "
United States
Susie J.
The price is CA $103
CA $397 total
includes taxes & fees
May 25 - May 26
Theatre District Condo | Gym • Free Parking • DT

A Cozy Cottage Near the Heart of All Louisville Attractions!

A Cozy Cottage Near the Heart of All Louisville Attractions!
Cloverleaf
10.0 out of 10, Exceptional, (390 reviews)
"Wonderful little place to stay for a weekend. 10/10 recommend staying here. Quiet and serene, and the hosts have thought of everything- very nicely equipped!"
United States
Amanda E.
The price is CA $198
CA $263 total
includes taxes & fees
May 25 - May 26
A Cozy Cottage Near the Heart of All Louisville Attractions!

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

Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
Jeffersonville
9.6 out of 10, Exceptional, (38 reviews)
"This little apartment was great for what we needed! Clean, efficient, fast communication with the host, and right on the river near cute shops and restaurants. The washer/dryer was a great bonus. "
United States
Courtney
The price is CA $76
CA $194 total
includes taxes & fees
May 21 - May 22
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
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?

Newly renovated 4BR CozySuites: You might want to consider this vacation rental near Crestwood, which is equipped with a garden, air-conditioning, and free WiFi to help you feel comfortable during your stay. It has 4 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 8 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 get outside and enjoy nature. Other places in town to visit include Oldham County Arts Center and South Oldham Library.

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.