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

1. Sleeps 8 • Fenced Yard and Firepit • 8 Minutes to Louisville

Sleeps 8 • Fenced Yard and Firepit • 8 Minutes to Louisville
Jeffersonville
The price is €300
includes taxes & fees
1 Sept - 2 Sept
Sleeps 8 • Fenced Yard and Firepit • 8 Minutes to Louisville

2. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
7.6 out of 10, Good, (4 reviews)
"Was great enjoyed our stay and time there"
United States
Tammy
The price is €96
includes taxes & fees
6 Sept - 7 Sept
StudioRes by Marriott Louisville East

3. 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, (86 reviews)
"Enjoyed the location and quiet neighborhood. You will not be one disappointed."
United States
Tania B.
The price is €302
includes taxes & fees
2 Sept - 3 Sept
Charming house in one of Louisville's most coveted neighborhoods

4. Near Highways and a 20 Min Drive to Louisville's Main Attractions

Near Highways and a 20 Min Drive to Louisville's Main Attractions
Louisville
10.0 out of 10, Exceptional, (57 reviews)
"Ross was super helpful from start to finish, and had plenty of space for our 14 guests to stay. This property would be very very high on my list to stay at again as a home base for a future Kentucky Derby weekend, or even a bourbon trail trip."
United States
Stephen Y.
The price is €329
includes taxes & fees
7 Sept - 8 Sept
Near Highways and a 20 Min Drive to Louisville's Main Attractions

5. 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, (26 reviews)
"Everything was outstanding!"
United States
John W.
The price is €250
includes taxes & fees
3 Sept - 4 Sept
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

6. Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Shelbyville
9.4 out of 10, Exceptional, (47 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is €200
includes taxes & fees
3 Sept - 4 Sept
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

7. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful location in a very nice small town. Grocery store, coffee shop and many other amenities close by.The property was very spacious and well done for 2 people."
United States
Kathleen S.
The price is €157
includes taxes & fees
1 Sept - 2 Sept
Unique Downtown Studio with an Industrial Vibe

8. Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Louisville
9.8 out of 10, Exceptional, (87 reviews)
"We had a great time! "
United States
Amber H.
The price is €977
includes taxes & fees
1 Sept - 2 Sept
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

9. Captain's Cabin Bed & Breakfast: Louder Than Life! Bourbon Trail History Romance

Captain's Cabin Bed & Breakfast: Louder Than Life! Bourbon Trail History Romance
Louisville
9.8 out of 10, Exceptional, (152 reviews)
"One of the most beautiful locations I've had the pleasure of staying in. Plan to book again in the future. So much historical value and comfort"
United States
Bill H.
The price is €349
includes taxes & fees
1 Sept - 2 Sept
Captain's Cabin Bed & Breakfast: Louder Than Life! Bourbon Trail History Romance

10. 3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms
La Grange
10.0 out of 10, Exceptional, (27 reviews)
"We had a wonderful stay!"
United States
Katie H.
The price is €933
includes taxes & fees
29 Sept - 30 Sept
3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

11. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.2 out of 10, Wonderful, (15 reviews)
"Lovely place, great outdoor seating areas, and spacious rooms."
United States
Joann E.
The price is €385
includes taxes & fees
1 Sept - 2 Sept
Beautiful restored Victorian farmhouse

12. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (54 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
The price is €154
includes taxes & fees
1 Sept - 2 Sept
The Bellwether Hotel

13. The Whiskey Stop! A Spacious Highlands Retreat

The Whiskey Stop! A Spacious Highlands Retreat
Germantown
10.0 out of 10, Exceptional, (78 reviews)
"It was perfect for our stay very comfortable and we enjoyed it very much"
United States
Lester W.
The price is €153
includes taxes & fees
1 Sept - 2 Sept
The Whiskey Stop! A Spacious Highlands Retreat

14. OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr

OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr
Hikes Point
10.0 out of 10, Exceptional, (67 reviews)
"Nice property close to attractions."
United States
Glenn C.
The price is €389
includes taxes & fees
7 Sept - 8 Sept
OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr

15. Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
9.8 out of 10, Exceptional, (27 reviews)
"Our stay was amazing! Beautiful porch for sitting outside on a rainy Kentucky night in late spring. The spa was delightful as well when it was raining. We stayed with our daughter and son in law, we look forward to bringing friends with us in the future."
United States
Laura O.
The price is €426
includes taxes & fees
1 Sept - 2 Sept
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

16. The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
Louisville
10.0 out of 10, Exceptional, (214 reviews)
"Beautiful location…very relaxing after a busy day!"
United States
Jim N.
The price is €374
includes taxes & fees
23 Sept - 24 Sept
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

17. Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
Crescent Hill
10.0 out of 10, Exceptional, (134 reviews)
"It was a great stay the property was super clean and the property manager was great!"
United States
Cole T.
The price is €207
includes taxes & fees
1 Sept - 2 Sept
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

18. 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, (24 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is €152
includes taxes & fees
1 Sept - 2 Sept
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

19. 2 Queen Beds|Nsmk,Micfridge

2 Queen Beds|Nsmk,Micfridge
Jeffersonville
10.0 out of 10, Exceptional, (272 reviews)
"Comfortable beds gave us good sleep each night,a key part of any trip!"
United States
Anonymous traveller
The price is €50
includes taxes & fees
13 Sept - 14 Sept
2 Queen Beds|Nsmk,Micfridge

20. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!
Belknap
The price is €230
includes taxes & fees
8 Sept - 9 Sept
Convenient & Cozy! Close to everything Louisville!
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 €96 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?

Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8: This holiday home rental outside of Crestwood is located on a lake, and has a fireplace, a balcony and a BBQ 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. You can relax into your holiday with 1 hot tub and a selection of books.

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.