A rural road flanked by trees and a wooden fence.

Crestwood Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Crestwood holiday rentals

Bar (on property)

Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (32 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 HK$706
HK$1,393 total
includes taxes & fees
19 Jul - 20 Jul
Unique Downtown Studio with an Industrial Vibe
TV

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, (20 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 HK$745
HK$1,436 total
includes taxes & fees
26 Jul - 27 Jul
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Coffee/tea maker, fridge, microwave, oven

Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (14 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is HK$1,729
HK$3,495 total
includes taxes & fees
20 Jul - 21 Jul
Beautiful restored Victorian farmhouse
Interior

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, (23 reviews)
"Everything was outstanding!"
United States
John W.
The price is HK$1,397
HK$2,195 total
includes taxes & fees
19 Jul - 20 Jul
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Free WiFi

2 Queen Beds|Nsmk,Micfridge

2 Queen Beds|Nsmk,Micfridge
Jeffersonville
10.0 out of 10, Exceptional, (269 reviews)
"Great staff that made checking in simple and painless,definitely would return if back in this area again."
United States
Anonymous traveller
The price is HK$501
HK$566 total
includes taxes & fees
20 Jul - 21 Jul
2 Queen Beds|Nsmk,Micfridge
Exterior

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
Bagdad
10.0 out of 10, Exceptional, (16 reviews)
"Great location and very clean. Plenty of room to spread out and relax. Carrie is a Professional and thoughtful host!!"
United States
David S.
The price is HK$3,048
HK$6,124 total
includes taxes & fees
19 Jul - 20 Jul
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
Exterior

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (12 reviews)
"The neighborhood is safe and we walked around to enjoy all the nearby shops and restaurants. Very quiet and peaceful, enjoyed the porch every morning."
United States
Stacy B.
The price is HK$564
HK$3,067 total
includes taxes & fees
20 Jul - 21 Jul
St. Matthew’s - Walk to Shops & Restaurants
Exterior

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, (149 reviews)
"Host were nice and friendly "
United States
Robert M.
The price is HK$1,799
HK$2,898 total
includes taxes & fees
21 Jul - 22 Jul
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Living area

Cozy Cottage House in Louisville

Cozy Cottage House in Louisville
Schnitzelburg
9.0 out of 10, Wonderful, (8 reviews)
"A cute and cozy cottage that is perfect for a weekend trip. Good atmosphere and good location near many restaurants. Hosts were welcoming and asked if we needed anything."
United States
John S.
The price is HK$694
HK$1,727 total
includes taxes & fees
26 Jul - 27 Jul
Cozy Cottage House in Louisville
Smart TV

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (40 reviews)
"It was a great stay"
United States
Jim M.
The price is HK$823
HK$2,111 total
includes taxes & fees
23 Jul - 24 Jul
Close to Everything in Louisville!!!
Interior

4th Street Suites - Opulent King Bed Suite

4th Street Suites - Opulent King Bed Suite
Downtown Louisville
10.0 out of 10, Exceptional, (26 reviews)
"Great location, attentive host. "
United States
Paul H.
The price is HK$550
HK$1,405 total
includes taxes & fees
22 Jul - 23 Jul
4th Street Suites - Opulent King Bed Suite
Outdoor spa tub

Hot Tub Speakeasy Game Room on Bourbon Trail

Hot Tub Speakeasy Game Room on Bourbon Trail
Shelbyville
10.0 out of 10, Exceptional, (21 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is HK$3,387
HK$4,300 total
includes taxes & fees
19 Jul - 20 Jul
Hot Tub Speakeasy Game Room on Bourbon Trail
Coffee/tea maker, fridge, microwave, oven

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, (23 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is HK$847
HK$1,267 total
includes taxes & fees
21 Jul - 22 Jul
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Smart TV, books

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, (43 reviews)
"Easy check in and check out. Nice stay. "
United States
Kelsey R.
The price is HK$627
HK$1,329 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
Interior

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, (41 reviews)
"Convenient location and great host"
United States
Bryan R.
The price is HK$533
HK$1,629 total
includes taxes & fees
2 Aug - 3 Aug
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
Smart TV

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, (48 reviews)
"Clean great location and host "
United States
Donna L.
The price is HK$651
HK$1,666 total
includes taxes & fees
9 Aug - 10 Aug
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
Interior

4th Street Suites - Beautiful King Bed Suite

4th Street Suites - Beautiful King Bed Suite
Downtown Louisville
9.6 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay here - Communication with Host was TOP NOTCH! "
United States
Kristy H.
The price is HK$550
HK$1,405 total
includes taxes & fees
3 Aug - 4 Aug
4th Street Suites - Beautiful King Bed Suite
Exterior

Luxury lodge in the heart of the Bluegrass

Luxury lodge in the heart of the Bluegrass
Waddy
10.0 out of 10, Exceptional, (9 reviews)
"Great property, nice location, well appointed. It is close to the interstate and with the leaves off, truck traffic could be heard from the top floor master bed. We would stay here again."
United States
Anonymous traveller
The price is HK$10,443
HK$16,457 total
includes taxes & fees
26 Jul - 27 Jul
Luxury lodge in the heart of the Bluegrass
Interior

4th Street Suites - Stunning King Bed Suite

4th Street Suites - Stunning King Bed Suite
Downtown Louisville
9.2 out of 10, Wonderful, (11 reviews)
"We loved our stay here! Property and room were very nice and clean! Room had everything you needed. Location was a very short walk to 4th street live and other attractions. We would stay here again! "
United States
Amy B.
The price is HK$550
HK$1,396 total
includes taxes & fees
21 Jul - 22 Jul
4th Street Suites - Stunning King Bed Suite
Coffee/tea maker, fridge, microwave, oven

Charming house in one of Louisville's most coveted neighborhoods

Charming house in one of Louisville's most coveted neighborhoods
Louisville
10.0 out of 10, Exceptional, (84 reviews)
"Home was great for a short stay. Kitchen fully furnished and all niceties such as coffee, snacks and toiletries. "
United States
Tony A.
The price is HK$1,482
HK$2,739 total
includes taxes & fees
21 Jul - 22 Jul
Charming house in one of Louisville's most coveted neighborhoods
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

Homewood Suites by Hilton Louisville Downtown, KY

Homewood Suites by Hilton Louisville Downtown, KY

10/10 Excellent
"Clean room"
David 2-night trip
Posted 1 hour ago
Homewood Suites by Hilton Louisville Downtown, KY

Find out more about Crestwood

Search for holiday rentals in Crestwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Crestwood using one of the methods below:

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Look no further and take a look at our great range of rental properties in Crestwood!

Frequently asked questions

Can I find a holiday rental in Crestwood?

Yes, there are holiday rentals in Crestwood close to Yew Dell Botanical Gardens, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Crestwood has to offer?

New! Welcome to the Jungle, Baby! 3br2ba Hot Tub!: This holiday home rental outside of Crestwood is located in the city centre, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Crestwood?

Expedia has 6 holiday 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 Kentucky Artisan Distillery and Oldham County Arts Center.

What’s a holiday rental in Crestwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Crestwood. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.