Holiday Rentals in Crestwood

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Our top choices for Crestwood holiday rentals

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 €369
includes taxes & fees
2 Mar - 3 Mar
Beautiful restored Victorian farmhouse

Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!

Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!
3.0 star property
New Albany
10.0 out of 10, Exceptional, (1 review)
"Amy was wonderful and went above and beyond to make sure we had a great stay. She even left pancakes w/syrup for breakfast and pasta w/sauce in case we didn’t have time to go to the store! It’s the small things that really stick out such as leaving a bowl of snacks, a few beers in the fridge, a bottle of wine, fully stocked medicine cabinet in case you forgot something. She even put food and water out for the dog along with toys and a blanket! We loved being there and it was such a beautiful...
United States
Robin
Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!

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 €161
includes taxes & fees
24 Mar - 25 Mar
Unique Downtown Studio with an Industrial Vibe

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)
"Awesome place, it was clean and spacious! "
United States
Ben M.
The price is €493
includes taxes & fees
29 Mar - 30 Mar
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 €159
includes taxes & fees
2 Mar - 3 Mar
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Private Home Close to Zoo, U of L, Churchill Downs

Private Home Close to Zoo, U of L, Churchill Downs
Poplar Level
9.6 out of 10, Exceptional, (24 reviews)
"This house was just as described. We had everything we needed and the property manager was awesome communicating the whole time. Would definitely recommend to anyone! "
United States
Renee C.
The price is €287
includes taxes & fees
2 Mar - 3 Mar
Private Home Close to Zoo, U of L, Churchill Downs

The Duke Hotel

The Duke Hotel
2.0 star property
Downtown Louisville
10.0 out of 10, Exceptional, (2 reviews)
"Room was comfortable. "
United States
Mary
The price is €119
includes taxes & fees
2 Mar - 3 Mar
The Duke Hotel

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
8.8 out of 10, Excellent, (38 reviews)
"Clean room, history and location. "
United States
RICHARD
The price is €112
includes taxes & fees
2 Mar - 3 Mar
The Bellwether Hotel

Germantown Fav! BOOK for Music Fests & DERBY 2026!

Germantown Fav! BOOK for Music Fests & DERBY 2026!
Germantown
10.0 out of 10, Exceptional, (72 reviews)
"The home was very clean, well stocked, and in a central location. We were extremely comfortable and found lots of things to do around town."
United States
Shannon W.
Germantown Fav! BOOK for Music Fests & DERBY 2026!

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, (14 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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 €226
includes taxes & fees
2 Mar - 3 Mar
Close to Everything in Louisville!!!

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (53 reviews)
"We loved our stay at this cottage. Very quiet and relaxing. We will definitely stay here again!"
United States
Jarrod H.
Carriage House, 7 minutes from downtown Louisville

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, (142 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 €339
includes taxes & fees
6 Mar - 7 Mar
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

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, (378 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 €165
includes taxes & fees
2 Mar - 3 Mar
A Cozy Cottage Near the Heart of All Louisville Attractions!

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)
"The cabin was cozy and inviting with so much history, and the grounds are meticulously maintained and absolutely gorgeous. Don was very nice to talk to and we enjoyed the 2 house pups that would let us pet them. "
United States
Adam H.
The price is €238
includes taxes & fees
2 Mar - 3 Mar
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Guests Love it! w/PrivPking-DERBY, Bourbon orWork!

Guests Love it! w/PrivPking-DERBY, Bourbon orWork!
Germantown
10.0 out of 10, Exceptional, (72 reviews)
"Super nice spot just perfect for two "
United States
Rick R.
The price is €201
includes taxes & fees
29 Mar - 30 Mar
Guests Love it! w/PrivPking-DERBY, Bourbon orWork!

Southern Family Charmer - Perfect Space & Location with style and comfort!

Southern Family Charmer - Perfect Space & Location with style and comfort!
Schnitzelburg
10.0 out of 10, Exceptional, (25 reviews)
"Good rooms and clean place"
United States
Mufid S.
Southern Family Charmer - Perfect Space & Location with style and comfort!

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 €125
includes taxes & fees
8 Mar - 9 Mar
Alfesco - Walkable Highlands Guesthouse

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

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (83 reviews)
"Great host beautiful house "
United States
Shantej G.
The price is €279
includes taxes & fees
2 Mar - 3 Mar
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

Secretariat Twin Spires Suite!

Secretariat Twin Spires Suite!
Jeffersonville
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place in a wonderful location. Walking distance to almost everything. Host was extremely helpful and made our stay unforgettable. The unit itself is very nice with easy access in and out. Lots of parking in the back. I would definitely recommend. "
United States
Drew J.
The price is €108
includes taxes & fees
15 Mar - 16 Mar
Secretariat Twin Spires Suite!
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 €112 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 South Oldham Library.

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.