Crestwood holiday lettings

We found 329 holiday rentals — enter your dates for availability

Discover a selection of 7 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.

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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)
  • Persimmon Ridge Golf Club (3.1 mi / 5 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:

  • Yew Dell Botanical Gardens (1.1 mi / 1.7 km)
  • 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)

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

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.
How much does it cost to rent a holiday home in Crestwood?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Crestwood to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Crestwood holiday house rentals?
You can find great discounts on house rentals in Crestwood on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Crestwood?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Crestwood holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Crestwood holiday rental?
Book your Crestwood holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Crestwood home rental booking on Vrbo?
To find Crestwood holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Crestwood holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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