A rural road flanked by trees and a wooden fence.

Holiday Rentals in Crestwood

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Our top choices for Crestwood holiday rentals

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 €159
includes taxes & fees
20 Jul - 21 Jul
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, (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 €164
includes taxes & fees
19 Jul - 20 Jul
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

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 €380
includes taxes & fees
20 Jul - 21 Jul
Beautiful restored Victorian farmhouse

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 €252
includes taxes & fees
19 Jul - 20 Jul
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

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 €63
includes taxes & fees
16 Aug - 17 Aug
2 Queen Beds|Nsmk,Micfridge

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

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 €349
includes taxes & fees
20 Jul - 21 Jul
St. Matthew’s - Walk to Shops & Restaurants

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 €327
includes taxes & fees
19 Jul - 20 Jul
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

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 €185
includes taxes & fees
20 Jul - 21 Jul
Cozy Cottage House in Louisville

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 €235
includes taxes & fees
6 Aug - 7 Aug
Close to Everything in Louisville!!!

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 €162
includes taxes & fees
22 Jul - 23 Jul
4th Street Suites - Opulent King Bed Suite

Bourbon Trail House with Hot Tub and Speakeasy

Bourbon Trail House with Hot Tub and Speakeasy
Shelbyville
10.0 out of 10, Exceptional, (21 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is €476
includes taxes & fees
19 Jul - 20 Jul
Bourbon Trail House with Hot Tub and Speakeasy

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 €145
includes taxes & fees
21 Jul - 22 Jul
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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, (42 reviews)
"Easy check in and check out. Nice stay. "
United States
Kelsey R.
The price is €152
includes taxes & fees
20 Jul - 21 Jul
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!

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 €184
includes taxes & fees
2 Aug - 3 Aug
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

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 €179
includes taxes & fees
10 Aug - 11 Aug
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

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 €160
includes taxes & fees
9 Aug - 10 Aug
4th Street Suites - Beautiful King Bed Suite

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 €1,819
includes taxes & fees
19 Jul - 20 Jul
Luxury lodge in the heart of the Bluegrass

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 €160
includes taxes & fees
21 Jul - 22 Jul
4th Street Suites - Stunning King Bed Suite

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 €303
includes taxes & fees
20 Jul - 21 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

Find out more about Crestwood

Everything you need to know about Crestwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Crestwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Crestwood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Crestwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Crestwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Crestwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Crestwood holiday rentals we have selected for you start as low as €124 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Crestwood rentals

At Expedia, we put the best Crestwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Crestwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Crestwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Crestwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville: This holiday home rental outside of Crestwood is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books 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.