Crestwood Vacation Rentals

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Our top choices for Crestwood vacation rentals

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 $130
CA $253 total
includes taxes & fees
May 18 - May 19
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 $475 total
includes taxes & fees
May 17 - May 18
Quiet Downtown Maple Cottage Gem

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 $159
CA $289 total
includes taxes & fees
May 20 - May 21
Unique Downtown Studio with an Industrial Vibe

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, (33 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 $239 total
includes taxes & fees
May 19 - May 20
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

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 $113
CA $268 total
includes taxes & fees
May 18 - May 19
Whiskey Stop-Close to Ky Expo, Walkable & Parking!

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (56 reviews)
"Amazing host! Great place to stay."
United States
Robert M.
The price is CA $185
CA $334 total
includes taxes & fees
May 16 - May 17
Carriage House, 7 minutes from downtown Louisville

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 $118
CA $560 total
includes taxes & fees
May 31 - Jun 1
St. Matthew’s - Walk to Shops & Restaurants

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.6 out of 10, Excellent, (11 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is CA $74
CA $196 total
includes taxes & fees
May 18 - May 19
Alfesco - Walkable Highlands Guesthouse

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)
"Great home and great location with access to many things close by."
United States
Todd S.
The price is CA $95
CA $271 total
includes taxes & fees
May 27 - May 28
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

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 $75
CA $239 total
includes taxes & fees
May 18 - May 19
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

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, (144 reviews)
"Very nice couple , will stay there again"
United States
Bryan S.
The price is CA $349
CA $555 total
includes taxes & fees
May 18 - May 19
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

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 $149
CA $223 total
includes taxes & fees
Jun 8 - Jun 9
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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 $244
CA $388 total
includes taxes & fees
May 19 - May 20
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

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 $314 total
includes taxes & fees
May 17 - May 18
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

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 $372 total
includes taxes & fees
May 17 - May 18
Close to Everything in Louisville!!!

Contemporary Studio in NuLu Arts District

Contemporary Studio in NuLu Arts District
Downtown Louisville
9.8 out of 10, Exceptional, (17 reviews)
"Very nice studio apartment, everything was clean with plenty of windows for natural light. Neighborhood was nice with plenty of restaurants within walking distance"
United States
John B.
The price is CA $74
CA $196 total
includes taxes & fees
Jun 1 - Jun 2
Contemporary Studio in NuLu Arts District

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, (37 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 $75
CA $194 total
includes taxes & fees
May 17 - May 18
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!

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 $197
CA $262 total
includes taxes & fees
May 18 - May 19
A Cozy Cottage Near the Heart of All Louisville Attractions!

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (47 reviews)
"Unique and beautiful hotel in a great area. Would highly recommend."
United States
Erika
The price is CA $184
CA $213 total
includes taxes & fees
Jun 1 - Jun 2
The Bellwether Hotel

Uptown Class

Uptown Class
New Albany
9.8 out of 10, Exceptional, (19 reviews)
"Great property. Good location. "
United States
Damont P.
The price is CA $171
CA $573 total
includes taxes & fees
May 17 - May 18
Uptown Class
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.