Crestwood Holiday Rentals

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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, (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 NZ$317
includes taxes & fees
7 Apr - 8 Apr
Unique Downtown Studio with an Industrial Vibe

Springtime in Kentucky, Cabin, Sleeps 29, Visit Bourbon Trail, Ark and Nature

Springtime in Kentucky, Cabin, Sleeps 29, Visit Bourbon Trail, Ark and Nature
Bagdad
9.6 out of 10, Exceptional, (248 reviews)
"Great cabin for large families. "
United States
Anonymous traveller
The price is NZ$1,052
includes taxes & fees
15 Apr - 16 Apr
Springtime in Kentucky, Cabin, Sleeps 29, Visit Bourbon Trail, Ark and Nature

Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (13 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is NZ$757
includes taxes & fees
2 Apr - 3 Apr
Beautiful restored Victorian farmhouse

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)
"Beautiful home and surroundings!"
United States
Peg H.
The price is NZ$878
includes taxes & fees
5 Apr - 6 Apr
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

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 NZ$319
includes taxes & fees
15 Apr - 16 Apr
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (9 reviews)
"It was everything we needed."
United States
Carmen C.
The price is NZ$458
includes taxes & fees
2 Apr - 3 Apr
St. Matthew’s - Walk to Shops & Restaurants

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, (26 reviews)
"Felix was a great host. Appreciated the texts. This is perfect for someone in Louisville for sports/derby. Could walk to them. Catholic Church down the street. "
United States
Beverly
The price is NZ$297
includes taxes & fees
5 Apr - 6 Apr
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

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, (15 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is NZ$264
includes taxes & fees
6 Apr - 7 Apr
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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, (32 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 NZ$299
includes taxes & fees
2 Apr - 3 Apr
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (37 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 NZ$467
includes taxes & fees
2 Apr - 3 Apr
Close to Everything in Louisville!!!

Close to Ky Fairgrounds&Expo, Churchill Downs!

Close to Ky Fairgrounds&Expo, Churchill Downs!
Germantown
10.0 out of 10, Exceptional, (74 reviews)
"The amenities were great and the house was the perfect spot for our weekend getaway. "
United States
Janessa D.
The price is NZ$349
includes taxes & fees
2 Apr - 3 Apr
Close to Ky Fairgrounds&Expo, Churchill Downs!

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 NZ$249
includes taxes & fees
5 Apr - 6 Apr
Alfesco - Walkable Highlands Guesthouse

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, (19 reviews)
"Everything was outstanding!"
United States
John W.
The price is NZ$485
includes taxes & fees
2 Apr - 3 Apr
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

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, (31 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 NZ$216
includes taxes & fees
6 Apr - 7 Apr
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!

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, (143 reviews)
"Great Trip…We enjoyed the four (4) nights. Host was great and her Scones were a treat."
United States
Anonymous traveller
The price is NZ$689
includes taxes & fees
4 Apr - 5 Apr
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

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, (40 reviews)
"Great home and great location with access to many things close by."
United States
Todd S.
The price is NZ$344
includes taxes & fees
6 Apr - 7 Apr
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (85 reviews)
"Very nice place"
United States
Seth B.
The price is NZ$636
includes taxes & fees
26 Apr - 27 Apr
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

Urban Explorer Pad | Near Downtown + Yard

Urban Explorer Pad | Near Downtown + Yard
Jeffersonville
9.0 out of 10, Wonderful, (42 reviews)
"Amazing stay, would stay again any time! Host was easy to communicate with and home was clean when we arrived and had everything needed for a wonderful stay!"
United States
Cameron J.
The price is NZ$625
includes taxes & fees
2 Apr - 3 Apr
Urban Explorer Pad | Near Downtown + Yard

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, (383 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 NZ$331
includes taxes & fees
4 Apr - 5 Apr
A Cozy Cottage Near the Heart of All Louisville Attractions!

Hot Tub, Bourbon Trail, Speakeasy, Firepit, GameRm

Hot Tub, Bourbon Trail, Speakeasy, Firepit, GameRm
Shelbyville
10.0 out of 10, Exceptional, (19 reviews)
"Overall great value and accommodations. Would highly recommend this property."
United States
Chad K.
The price is NZ$1,051
includes taxes & fees
15 Apr - 16 Apr
Hot Tub, Bourbon Trail, Speakeasy, Firepit, GameRm
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, 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 NZ$271 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?

Spacious 4-bedroom townhome with 2 car garage in perfect Louisville location: This holiday home rental outside of Crestwood offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in Crestwood?

Expedia has 7 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.