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, (14 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is €375
includes taxes & fees
3 Jun - 4 Jun
Beautiful restored Victorian farmhouse

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 €161
includes taxes & fees
8 Jun - 9 Jun
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

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 €157
includes taxes & fees
3 Jun - 4 Jun
Unique Downtown Studio with an Industrial Vibe

Whiskey Stop-Close to Ky Expo, Walkable & Parking!

Whiskey Stop-Close to Ky Expo, Walkable & Parking!
Louisville
10.0 out of 10, Exceptional, (77 reviews)
"The amenities were great and the house was the perfect spot for our weekend getaway. "
United States
Janessa D.
The price is €180
includes taxes & fees
9 Jun - 10 Jun
Whiskey Stop-Close to Ky Expo, Walkable & Parking!

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, (54 reviews)
"Great place!"
United States
Nakoma F.
The price is €316
includes taxes & fees
3 Jun - 4 Jun
Near Highways and a 20 Min Drive to Louisville's Main Attractions

Preston Retreat - Convenient Germantown Location

Preston Retreat - Convenient Germantown Location
Merriwether
8.2 out of 10, Very good, (13 reviews)
"Not sure what happened to the access code that didn't work and we had to contact the host for a new one. Otherwise, it was clean and the beds were comfy. Having two bathrooms was a plus. "
United States
Donald S.
The price is €186
includes taxes & fees
3 Jun - 4 Jun
Preston Retreat - Convenient Germantown Location

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (49 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
The price is €142
includes taxes & fees
8 Jun - 9 Jun
The Bellwether Hotel

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, (46 reviews)
"Clean great location and host "
United States
Donna L.
The price is €173
includes taxes & fees
10 Jun - 11 Jun
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

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, (20 reviews)
"Everything was outstanding!"
United States
John W.
The price is €244
includes taxes & fees
10 Jun - 11 Jun
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Shelby Park
9.6 out of 10, Exceptional, (24 reviews)
"This home is warm and cozy and close to everything we had planned."
United States
Dawn G.
The price is €198
includes taxes & fees
3 Jun - 4 Jun
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

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

Guests Love it! w/PrivPking-Bourbon, Music orWork!
Louisville
10.0 out of 10, Exceptional, (78 reviews)
"An excellent place to stay. Easy parking- excellent communication by the host and a quiet place to stay. The location was perfect in relation to what we wanted to see and do! "
United States
Jessica H.
The price is €173
includes taxes & fees
4 Jun - 5 Jun
Guests Love it! w/PrivPking-Bourbon, Music orWork!

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (39 reviews)
"Everything about our stay was excellent."
United States
James H.
The price is €232
includes taxes & fees
3 Jun - 4 Jun
Close to Everything in Louisville!!!

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
9.8 out of 10, Exceptional, (37 reviews)
"The host was very welcoming! Thank you for a wonderful stay! "
United States
bevin o.
The price is €192
includes taxes & fees
21 Jun - 22 Jun
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, (20 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is €138
includes taxes & fees
29 Jun - 30 Jun
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (10 reviews)
"It was everything we needed."
United States
Carmen C.
The price is €382
includes taxes & fees
30 Jun - 1 Jul
St. Matthew’s - Walk to Shops & Restaurants

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, (33 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 €153
includes taxes & fees
3 Jun - 4 Jun
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE
Louisville
10.0 out of 10, Exceptional, (84 reviews)
"Host was accommodating and welcoming. "
United States
Bobbie S.
The price is €212
includes taxes & fees
8 Jun - 9 Jun
Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

Contemporary Studio in NuLu Arts District

Contemporary Studio in NuLu Arts District
Downtown Louisville
9.8 out of 10, Exceptional, (17 reviews)
"Matt communicated well and was always on top of anything we asked for. Great location and great apartment!! Will definitely stay here again."
United States
Stacey W.
The price is €127
includes taxes & fees
3 Jun - 4 Jun
Contemporary Studio in NuLu Arts District

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, (126 reviews)
"Really nice unit. Very comfortable and clean. Very nice area -"
United States
Harry
The price is €207
includes taxes & fees
4 Jun - 5 Jun
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

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, (147 reviews)
"Very nice couple , will stay there again"
United States
Bryan S.
The price is €347
includes taxes & fees
7 Jun - 8 Jun
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
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 €127 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?

Charming Highlands Carriage House 2 beds/2bath NO POOL: This holiday home rental outside of Crestwood offers a balcony, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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.