Crestwood holiday homes

We found 204 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Crestwood to find one that's perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, which might include a garden and hot tub. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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Why people love visiting friendly Crestwood

Enjoy the entertainment and other features of Crestwood. This welcoming and romantic city entices travellers with its restaurants and shopping. McCormick Place and Soldier Field are just a couple of the must-see attractions in the area. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Crestwood

Are you hoping to discover top things to see and do while you're in the area? 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. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Ravisloe Country Club (8.1 mi / 13.1 km)
  • Harborside International Golf Center (8.4 mi / 13.5 km)
  • Cog Hill Golf & Country Club (10.3 mi / 16.6 km)
  • Galloping Ghost (12 mi / 19.3 km)
  • Oak Brook Golf Course (15.4 mi / 24.7 km)
  • Village Green (4.4 mi / 7.1 km)

Exploring the natural features in Crestwood

Whether you're an active traveller or just want to spend some time taking in the scenery, Crestwood is a great place to get out in nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Lake Katherine Nature Center (3 mi / 4.8 km)
  • Abbott Park (7.9 mi / 12.6 km)
  • Midway Plaisance (11.6 mi / 18.6 km)
  • Washington Park (11.8 mi / 19 km)
  • Jackson Park (12.1 mi / 19.4 km)
  • Calumet Park (12.2 mi / 19.7 km)

Transport to and around Crestwood

The nearest airport is in Chicago Midway Airport (MDW), located 8.8 mi (14.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Chicago O'Hare International Airport (ORD), which is 23.2 mi (37.3 km) away.

Frequently asked questions

What is the best area to stay in Crestwood when booking a holiday rental?
In Crestwood, Illinois, one of the best areas to consider for a holiday rental is near the vibrant community centre, which serves as a hub for local events and activities. This area offers a variety of rental properties, making it a convenient choice for visitors looking to immerse themselves in the local culture.A short drive away, you'll find the beautiful Tinley Creek Forest Preserve, superb for outdoor enthusiasts who enjoy hiking and nature walks. The scenic trails and picnic spots provide a lovely escape for families or solo travellers looking to unwind amidst nature.Additionally, staying closer to the commercial district means easy access to a range of dining options and shopping experiences. The local eateries offer a taste of the region's culinary delights, making it a pleasant area for those who appreciate good food.
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 several available throughout the area. These properties typically feature spacious layouts, often including multiple bedrooms and fully equipped kitchens, making them ideal for families or groups. Many of these homes also come with outdoor spaces, such as gardens or patios, providing a comfortable environment for relaxation after a day of exploring the local attractions.
Are there any family house rentals in Crestwood?
In Crestwood, Illinois, there are several family-friendly house rentals available, making it a great choice for those travelling with children. This suburban area features spacious homes, often equipped with multiple bedrooms and ample living space for families to relax together. Many properties include kitchens, allowing visitors to prepare meals during their stay, and comfortable dining areas for shared family dinners.Crestwood is conveniently located near various parks and recreational facilities, which are great for outdoor activities. For instance, nearby parks often offer playgrounds, sports courts, and picnic areas, providing plenty of opportunities for family fun. The locale also has shopping centres and dining options within easy reach, ensuring that families have everything they need for a pleasant visit.
Are there pet-friendly house rentals in Crestwood?
In Crestwood, there are several pet-friendly house rentals available, offering a range of amenities to ensure a comfortable stay for both you and your furry companions. Many of these properties feature spacious living areas, fully equipped kitchens, and outdoor spaces, such as private gardens or patios, where pets can enjoy the fresh air.The proximity to local parks, including the nearby Crestwood Park, provides ample opportunities for walks and outdoor playtime with your pets. This park features walking trails and open green spaces, making it a lovely spot for leisurely strolls. Additionally, the area has pet-friendly cafes and shops, allowing you to explore the local scene while bringing your pets along.
Are there any remote work holiday rentals in Crestwood?
In Crestwood, Illinois, there are several remote work holiday rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties offer essential remote work amenities, including high-speed internet access and Wi-Fi, ensuring a productive environment during your stay.Travellers can expect comfortable accommodations that often feature dedicated workspaces, allowing for a seamless transition between work and relaxation. Additionally, the area is conveniently located near local parks and amenities, providing opportunities for outdoor breaks and local exploration. 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, which allow guests to prepare their own meals conveniently. Onsite parking is also a common feature, making it easy for travellers with vehicles to access their accommodations. Many properties in the area are pet-friendly, permitting both pets and service animals, which is ideal for those travelling with furry companions. Additionally, some rentals come with a blender, suiting guests who wish to whip up smoothies or other blended drinks during their stay.
When is the best time to visit Crestwood for a holiday rental?
The peak season for holiday rentals in Crestwood is from May to July, with July being the most popular month for visitors. This vibrant period attracts families and outdoor enthusiasts who revel in the warm weather and numerous local events, making it an ideal time for exploring the scenic parks and recreational areas.During these summer months, you can expect temperatures typically ranging from the mid-teens to low 30s Celsius, providing a comfortable climate for outdoor activities such as hiking or picnicking. Crestwood boasts several lovely parks, great for leisurely strolls or family gatherings, ensuring a delightful experience for all.For those looking for a more budget-friendly option, consider visiting in November. While the weather is cooler, with temperatures around 0 to 10 degrees Celsius, this month offers a tranquil atmosphere great for exploring indoor attractions, local shops, and enjoying the local cuisine without the crowds.
What are the top attractions in Crestwood?
In Crestwood, visitors can explore a variety of attractions that cater to different interests. The local parks, such as the Crestwood Park, offer ample green space for outdoor activities, walking trails, and playgrounds great for families. The nearby Chicago Ridge Mall provides shopping options and dining experiences, making it a popular spot for locals and visitors alike.For those interested in history, the area is close to the Tinley Creek Trail, which features scenic views and opportunities for biking and hiking.
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.