Crestwood holiday homes

We found 301 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Crestwood that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Crestwood

Showing deals for:4 Dec - 11 Dec

Dining
Exterior
Interior
Living area
9.6/10Exceptional (10 reviews)

4Br Home on Sabre Hill Horse Farm 25 acres ~ Bourbon Trail

Simpsonville

8% off
NZ$6,832
NZ$976 per night
includes taxes & fees
4Br Home on Sabre Hill Horse Farm 25 acres ~ Bourbon Trail
Terrace/patio
Exterior
Dining
Private kitchen
10/10Exceptional (11 reviews)

Castle St Matthews

Louisville

8% off
NZ$15,476
NZ$2,211 per night
includes taxes & fees
Castle St Matthews
Foyer as you walk in front door
Exterior
Family room off of foyer and next to Living room area 1 with queen bed And bunks
Living room area 1 with queen bed and bunk beds
9.8/10Exceptional (14 reviews)

Beautiful views and sunrises overlooking the water. Spacious home with elevator.

Jeffersonville

19% off
NZ$6,663
NZ$952 per night
includes taxes & fees
Beautiful views and sunrises overlooking the water. Spacious home with elevator.
Private kitchen
Living area
Living area
Enjoy the sunrise over the river from the enclosed sunroom
10/10Exceptional (29 reviews)

Fully Remodeled Exquisite Louisville Area Tranquil Riverfront Home!

Jeffersonville

8% off
NZ$5,714
NZ$816 per night
includes taxes & fees
Fully Remodeled Exquisite Louisville Area Tranquil Riverfront Home!
Living area
Exterior
Terrace/patio
Property grounds
9.8/10Exceptional (87 reviews)

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

Louisville

7% off
NZ$12,868
NZ$1,838 per night
includes taxes & fees
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Property grounds
Pool
Living area
Exterior
10/10Exceptional (11 reviews)

Safe, scenic, and convenient. Bordering a State Park!

Louisville

13% off
NZ$6,771
NZ$967 per night
includes taxes & fees
Safe, scenic, and convenient. Bordering a State Park!
Front of the home.
Living Room, Breakfast area. Kitchen is to the right.
Walkout basement sleeping area. Note: This is an Unfinished Basement.
Friendly front porch.
10/10Exceptional (57 reviews)

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

Louisville

7% off
NZ$4,862
NZ$695 per night
includes taxes & fees
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Pool
Private kitchen
Kitchen
Interior
9.6/10Exceptional (24 reviews)

Spacious 5BR Getaway – Pool, Patios & Fun

Louisville

7% off
NZ$14,192
NZ$2,027 per night
includes taxes & fees
Spacious 5BR Getaway – Pool, Patios & Fun
Interior
Outdoor spa tub
Living area
Room
10/10Exceptional (17 reviews)

King Bed-Hot Tub-Arcade! Perfect for couples and families. Close to I-71.

La Grange

16% off
NZ$2,564
NZ$366 per night
includes taxes & fees
King Bed-Hot Tub-Arcade! Perfect for couples and families. Close to I-71.
Interior
Exterior
Interior
Private kitchen
10/10Exceptional (6 reviews)

3-bedroom condo in Norton Commons

Prospect

8% off
NZ$4,365
NZ$624 per night
includes taxes & fees
3-bedroom condo in Norton Commons
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Crestwood getaway

Learn about the unique charm of Crestwood with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Crestwood

Do you want to find things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Crestwood a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Valhalla Golf Club (5.6 mi / 9.1 km)
  • Louisville Zoo (15.1 mi / 24.2 km)
  • Kentucky Kingdom (17.3 mi / 27.9 km)
  • Churchill Downs (18.2 mi / 29.2 km)
  • Covered Bridge Golf Club (19.3 mi / 31.1 km)
  • Polo Fields Golf and Country Club (4.8 mi / 7.7 km)

Exploring the natural features in Crestwood

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Crestwood is a great place to spend some time outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • E.P. Tom Sawyer State Park (5.6 mi / 8.9 km)
  • Beckley Creek Park (7.9 mi / 12.7 km)
  • Ohio River Valley (11.6 mi / 18.7 km)
  • Cherokee Park (13.4 mi / 21.6 km)
  • Louisville Waterfront Park (14 mi / 22.6 km)
  • Big Four Bridge (15 mi / 24.2 km)

How to get to and around Crestwood

The nearest airport is in Louisville, KY (LOU-Bowman Field), located 12.7 mi (20.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Louisville International Airport (SDF), which is 17.5 mi (28.1 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Crestwood?
The average price for a holiday home in Crestwood is based on a number of factors, like property type, length of stay and season. Whether you prefer a sprawling house with room for friends and family or a cosy cabin for just you and your sweetheart, just add your travel dates to view stays with amazing value.
How much does it cost to rent a beach house in Crestwood?
Prices for beach houses in Crestwood vary depending on the type and size of the property and when you're travelling. Just enter your travel dates into Bookabach and the number of guests to view available options and prices. From there you can use the filters to tailor your search by ratings, amenities and more.
What are the top attractions for families in Crestwood?
You'll find loads of fabulous things to see and do with the family in Crestwood, including:
  • Danger Run
  • Yew Dell Botanical Gardens
  • LaGrange Main Street Visitor Centre
How old do you have to be to rent a holiday home in Crestwood?
We recommend checking with the Crestwood holiday home you're looking at on Bookabach as the age limit differs. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Crestwood for?
How long you can book a holiday home in Crestwood varies according to the property. Just enter your desired dates to view a list of options offering extended stays. With a range of creature comforts such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to get somewhere perfect to call your home away from home in Crestwood.