Crestwood holiday homes

We found 304 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:22 Jan - 29 Jan

Dining
Exterior
Interior
Living area
Exceptional
(14 reviews)

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

Simpsonville

8% off
NZ$6,948
for 7 nights, 1 room
NZ$993 per night
includes taxes & fees
4Br Home on Sabre Hill Horse Farm 25 acres ~ Bourbon Trail
Living area
Exterior
Terrace/patio
Interior
Exceptional
(87 reviews)

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

Louisville

7% off
NZ$10,736
for 7 nights, 1 home
NZ$1,534 per night
includes taxes & fees
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Living area
Exterior
Terrace/patio
Dining
Exceptional
(12 reviews)

Castle St Matthews

Louisville

8% off
NZ$16,115
for 7 nights, 1 home
NZ$2,302 per night
includes taxes & fees
Castle St Matthews
Family room off of foyer and next to Living room area 1 with queen bed And bunks
Exterior
Living room area 1 with queen bed and bunk beds
Terrace/patio
Exceptional
(14 reviews)

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

Jeffersonville

16% off
NZ$7,477
for 7 nights, 1 home
NZ$1,068 per night
includes taxes & fees
Beautiful views and sunrises overlooking the water. Spacious home with elevator.
New separete entrance to a new addition
Private kitchen
Interior
Kitchen
Exceptional
(26 reviews)

Spacious 5BR Getaway – Pool, Patios & Fun

Louisville

8% off
NZ$14,173
for 7 nights, 1 home
NZ$2,025 per night
includes taxes & fees
Spacious 5BR Getaway – Pool, Patios & Fun
Kitchen view 3
Kitchen view 2
Terrace/patio
Dining room view 1
Exceptional
(52 reviews)

Unique Serenity - Entire Home On Private 3-Acres in Metro. Expo Center, Bourbon

Louisville

8% off
NZ$5,566
for 7 nights, 1 home
NZ$795 per night
includes taxes & fees
Unique Serenity - Entire Home On Private 3-Acres in Metro. Expo Center, Bourbon
Interior
Exterior
Interior
Dining
Exceptional
(6 reviews)

3-bedroom condo in Norton Commons

Prospect

8% off
NZ$4,492
for 7 nights, 1 apartment
NZ$642 per night
includes taxes & fees
3-bedroom condo in Norton Commons
Living area
Pool
Exterior
Living area
Exceptional
(11 reviews)

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

Louisville

13% off
NZ$6,880
for 7 nights, 1 home
NZ$983 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.
Catwalk adjoins the upstairs bedrooms.
Friendly front porch.
Exceptional
(58 reviews)

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

Louisville

8% off
NZ$5,037
for 7 nights, 1 home
NZ$720 per night
includes taxes & fees
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Dining
Private kitchen
Living area
Room
Exceptional
(35 reviews)

❤️Stay at Peppermint Cottage - Norton Commons -Walk eat & shop- free breakfast

Prospect

16% off
NZ$4,646
for 7 nights, 1 home
NZ$664 per night
includes taxes & fees
❤️Stay at Peppermint Cottage - Norton Commons -Walk eat & shop- free breakfast
Living area
Exterior
Interior
Room
Exceptional
(6 reviews)

Charming 4 bedroom home minutes from Downtown!

Jeffersonville

16% off
NZ$2,868
for 7 nights, 1 home
NZ$410 per night
includes taxes & fees
Charming 4 bedroom home minutes from Downtown!
Interior
Outdoor spa tub
Private kitchen
Living area
Exceptional
(19 reviews)

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

La Grange

16% off
NZ$2,608
for 7 nights, 1 home
NZ$373 per night
includes taxes & fees
King Bed-Hot Tub-Arcade! Perfect for couples and families. Close to I-71.

  • 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 International Airport (SDF), located 17.5 mi (28.1 km) from the city centre.

Frequently asked questions

What is the best area to stay in Crestwood when booking a holiday rental?
When considering a holiday rental in Crestwood, Kentucky, a popular area to stay is in the vicinity of the Oldham County area. This neighbourhood offers a charming suburban atmosphere with a friendly community vibe. It's a fantastic spot for those looking to enjoy a peaceful retreat while still having access to local amenities.Nearby, you can explore the beautiful Yew Dell Botanical Gardens, which features stunning landscapes and a variety of plant collections, superb for nature lovers. Additionally, the historic town of La Grange is just a short drive away and is known for its quaint shops and delightful dining options, making it a lovely place to spend an afternoon.In terms of accommodation, Crestwood has a range of properties, including cosy cottages and modern homes, suiting different preferences and group sizes.
What is the most popular type of holiday rental accomodation in Crestwood?
In Crestwood, holiday houses are the most popular type of holiday rental, with around 10 available in the area. These homes provide ample space, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Additionally, there are several charming cottages scattered throughout the neighbourhood, offering a cozier, more intimate atmosphere. Many of these rentals are set in peaceful surroundings, great for those looking to relax while enjoying the local scenery.
Are there any family house rentals in Crestwood?
In Crestwood, Kentucky, there are several family-friendly house rentals available, making it an excellent choice for families seeking a comfortable stay. Visitors can find homes in pleasant neighbourhoods that offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces ideal for children to play. Many properties also come with conveniences such as Wi-Fi and air conditioning, ensuring a comfortable experience.The locale is in close proximity to attractions like the historic Oldham County Courthouse and the scenic parks that provide opportunities for outdoor activities. Families can enjoy the surrounding natural beauty while staying in well-appointed accommodations that cater to their needs.
Can I rent a holiday home with a pool or hot tub in Crestwood?
In Crestwood, Kentucky, there are several holiday homes available for rent that feature pools or hot tubs, providing a great opportunity for relaxation and enjoyment. This charming suburb, located just a short drive from the bustling city of Louisville, offers a variety of rental options in its scenic neighbourhoods.Travellers can expect amenities such as private pools, hot tubs, outdoor entertainment areas, and fully equipped kitchens, making these properties ideal for both family gatherings and quiet retreats. Many rentals also include spacious living areas and comfortable bedrooms, ensuring a pleasant stay. Additionally, the surrounding area boasts local parks and recreational facilities, adding to the appeal for those seeking outdoor activities.
Are there pet-friendly house rentals in Crestwood?
In Crestwood, Kentucky, there are several pet-friendly house rentals available, making it a suitable destination for travellers with pets. Many of these holiday homes are equipped with amenities such as spacious backyards, allowing pets to roam freely, and modern kitchens for convenient self-catering. You can expect comfortable living areas, often with features like outdoor patios or decks, great for enjoying the pleasant Kentucky weather.The neighbourhood itself offers a tranquil, suburban atmosphere, which is ideal for leisurely strolls with your furry companions. Nearby parks and green spaces provide additional opportunities for outdoor activities, ensuring that both you and your pets can enjoy the natural surroundings.
Are there any remote work holiday rentals in Crestwood?
In Crestwood, Kentucky, there are several remote work-friendly holiday rentals available, with around 10 options to choose from. These properties cater specifically to those who need to balance work and leisure, offering amenities such as dedicated desk spaces, comfortable desk chairs, and high-speed Wi-Fi to ensure a productive environment. Many rentals also provide access to printers, making it convenient for business-related tasks.The area itself is known for its suburban charm, with nearby parks and recreational areas that allow for a refreshing break after work hours. Crestwood's close proximity to local shops and dining options further enhances the appeal for those looking to combine a work trip with some relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Crestwood?
In Crestwood, popular rental amenities include well-equipped kitchens, allowing guests to prepare meals at their convenience. Many properties also feature onsite parking, making it easy for travellers with vehicles. For those who enjoy a warm drink, rentals often come with coffee and tea makers, as well as blenders for smoothie enthusiasts. Additionally, outdoor spaces like decks or patios are common, providing a pleasant area for relaxation and enjoying the surrounding scenery.
When is the best time to visit Crestwood for a holiday rental?
April marks the beginning of the peak season in Crestwood, Kentucky, as visitors flock to this charming town to enjoy the blossoming scenery and vibrant local events. The months from April to June are particularly popular, with pleasant weather encouraging outdoor activities and sightseeing. During this time, temperatures typically range from 10 to 20 degrees Celsius, making it ideal for exploring the picturesque parks and enjoying leisurely walks in the refreshing spring air.April is especially enticing, as it offers a delightful blend of mild temperatures and blooming flora, great for those keen on immersing themselves in nature. The town comes alive with various community events and festivals that celebrate the season, providing an excellent opportunity to connect with locals and experience the unique culture of Crestwood.For travellers looking to enjoy Crestwood on a budget, consider planning your visit in January. While this month is less busy, it offers its own charm with a quieter atmosphere, allowing for a more intimate experience of the town's history and attractions.Ultimately, your choice of when to visit Crestwood will depend on whether you prefer the lively energy of the peak season filled with outdoor adventures and community festivities or the tranquil, reflective beauty of the quieter months.
Are all fees included in the Crestwood holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Crestwood holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Crestwood with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Crestwood holiday homes?
You can find great discounts on holiday homes in Crestwood on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Crestwood holiday home booking on Bookabach?
To find Crestwood holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Crestwood?
A long-stay holiday home in Crestwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Crestwood holiday home?
Book your Crestwood holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Crestwood?
Prices for holiday homes in Crestwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Crestwood to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.