Photo by Michelle E

Chesterfield holiday homes

We found 1,533 holiday rentals — enter your dates for availability

Discover a selection of 14 apartments and other holiday rentals in Chesterfield that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and a TV. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Chesterfield

Showing deals for:26 Dec - 2 Jan
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Why visit Chesterfield

  • Vibrant Chesterfield Village: Experience the lively atmosphere, unique shops, and dining options in this charming area.
  • Chesterfield Mall: A fantastic shopping destination offering a wide range of retail stores and eateries for a fun day out.
  • Outdoor Adventures: Explore the nearby national and state parks, perfect for hiking, picnicking, and enjoying nature.
  • Rich Local History: Visit the Chesterfield Court House to learn about the town’s fascinating past.
  • Family-Friendly Activities: Chesterfield is an ideal spot for families, with plenty of attractions and friendly locals to enhance your visit.

Top attractions near Chesterfield

Chesterfield, Missouri, is a fantastic spot for families and those seeking entertainment or city experiences. You can explore the vibrant Chesterfield Village and Chesterfield Mall, delve into the area's history, or enjoy the scenic national and state parks nearby. Don't miss the chance to visit the Chesterfield Court House and discover the charm of western Chesterfield while soaking up the local culture and outdoor activities that this lovely town has to offer.

  • Six Flags St. Louis: This thrilling amusement park, located 19.3km from Chesterfield, boasts a variety of rides and attractions for the whole family, offering an exhilarating outdoor adventure experience.
  • Magic House - St. Louis Children's Museum: Only 16.1km away, this interactive children's museum provides a fun-filled environment where families can explore, learn, and engage in hands-on activities that nurture creativity and curiosity.
  • Hollywood Casino Amphitheatre: Situated 12.9km from Chesterfield, this vibrant entertainment venue hosts a range of concerts and events, making it a fantastic spot for family enjoyment and memorable experiences.

Things to do recommended for couples

Searching for a romantic getaway in Chesterfield? Start your adventure at Bellerive Country Club for a touch of luxury, then enjoy live entertainment at The Factory. For some winter fun, head to Hidden Valley Ski Resort, just 16.1km away, for a thrilling ski experience together.

Things to do recommended for families

Your family will have a blast at Lou Fusz Soccer Complex, just 6.4km away, embracing the sports vibe. Enjoy adventure at Chesterfield Sports Fusion nearby, or skate at the Centene Community Ice Center, located 12.9km away, perfect for sports and entertainment.

Things to do recommended for groups

Enjoy a shopping spree at St. Louis Premium Outlets, explore the scenic Missouri Bluffs Golf Course for a round of golf, or visit Fast Lane Classic Cars to admire vintage vehicles. These activities offer a fantastic local experience for your group in Chesterfield.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chesterfield

If you're heading off with a group, a family, or even your pets, or if you're considering a longer stay, be sure to refine your search according to your key priorities. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Chesterfield with a group: Think about how many bedrooms you'll require, as well as any amenities like a complete kitchen or outdoor area for group activities. Thankfully, you can easily filter for these features and more on Vrbo.
  • Traveling to Chesterfield with young kids: Journeying with young kids can be quite a task. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly activities.
  • Taking your pets with you to Chesterfield: For many, a family holiday isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly options come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Chesterfield: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Chesterfield

Chesterfield, Missouri, offers a delightful blend of family-friendly attractions and scenic spots perfect for a memorable holiday. Explore charming neighbourhoods with friendly locals, enjoy the stunning landscapes, and discover nearby cities that are rich in history and romance. With its vibrant atmosphere and excellent school districts, Chesterfield is an ideal destination for families seeking both entertainment and relaxation. Experience the warmth of this gorgeous city on your next adventure.

  • St. Louis: St. Louis is a vibrant metropolis located near Chesterfield, offering a dynamic blend of family-friendly and city-themed experiences. Known for its iconic Gateway Arch, St. Louis boasts a plethora of attractions including sports stadiums, event venues, and an array of entertainment options like arcade adventure zones. Visitors can explore the lively downtown area, enjoy arena events, or immerse themselves in local culture at museums and parks. With its rich history and bustling atmosphere, St. Louis is a must-visit for those seeking an exciting urban adventure.
  • St. Charles: Just 16.1km from Chesterfield, St. Charles is a charming city renowned for its romantic ambiance and family-oriented activities. The historic district is a highlight, featuring quaint shops and delightful eateries. Visitors can enjoy a range of entertainment options, from theatres to shopping malls. With landmarks like event venues and historical sites, St. Charles invites travellers to experience its unique blend of nostalgia and modern conveniences, making it a perfect spot for both couples and families looking for a delightful day out.
  • Winchester: Winchester is a quaint village located 8.0km from Chesterfield, ideal for families and adventure seekers. Known for its outdoor experiences, visitors can enjoy thrilling activities at nearby amusement parks and arcade adventure zones. The village is home to attractions like a children's museum and a theme park, ensuring fun for all ages. With its serene environment and close-knit community feel, Winchester offers a relaxing escape, making it perfect for those looking to unwind and enjoy some quality family time.

Best time to go to Chesterfield

If you're planning a trip to Chesterfield, it's a good idea to check both the weather and property rates. The warmest month is July.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.6°F (-0.2°C)Light RainMostly CloudyAverage
February34.7°F (1.5°C)Light RainMostly SunnyAverage
March46.4°F (8.0°C)Light RainMostly SunnyAverage
April55.9°F (13.3°C)Light RainMostly SunnySlightly High
May66.2°F (19.0°C)Light RainMostly SunnyAverage
June75.9°F (24.4°C)Light RainMostly SunnySlightly High
July79.0°F (26.1°C)Light RainMostly SunnySlightly High
August77.2°F (25.1°C)Light RainMostly SunnyAverage
September70.9°F (21.6°C)Light RainMostly SunnyAverage
October58.5°F (14.7°C)Light RainMostly SunnySlightly Low
November46.2°F (7.9°C)Light RainMostly SunnySlightly Low
December37.6°F (3.1°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a real difference, as prices can fluctuate. You might also find considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of holiday rental. We're here to help you find the perfect spot for your getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and organise your travel arrangements. You can find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

The friendly city of Chesterfield awaits you

Enjoy the museums and other features of Chesterfield. This city's shopping, restaurants and sporting events attract many visitors, as does its welcoming and scenic location. 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 Chesterfield

Do you want to discover attractions to see in the area? Venture out of your holiday home and experience everything that makes Chesterfield a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Chesterfield Sports Fusion (2.8 mi / 4.6 km)
  • Missouri Bluffs Golf Course (6.6 mi / 10.6 km)
  • Hidden Valley Ski Resort (9.9 mi / 15.9 km)
  • Six Flags St. Louis (11.7 mi / 18.9 km)
  • Chandler Hill Vineyards (12.9 mi / 20.8 km)
  • Grant's Farm (13.7 mi / 22.1 km)

Exploring the natural features in Chesterfield

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Chesterfield is a great place to spend some time outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Lou Fusz Soccer Complex (4.4 mi / 7.2 km)
  • Lone Elk Park (9 mi / 14.5 km)
  • Kirkwood Park (9.5 mi / 15.3 km)
  • Katy Trail (10.3 mi / 16.6 km)
  • August A. Busch Memorial Conservation Area (11.1 mi / 17.8 km)
  • Laumeier Sculpture Park (11.3 mi / 18.1 km)

Transport options to and around Chesterfield

The nearest airport is in St. Louis, MO (SUS-Spirit of St. Louis), located 4.4 mi (7 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Lambert-St. Louis International Airport (STL), which is 12.1 mi (19.4 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Chesterfield?
The most in-demand types of holiday homes in Chesterfield are houses. Looking for something different? Bookabach offers a variety of options to match our guests' unique needs, so you'll see holiday properties in loads of shapes and sizes. The perfect fit is waiting for you — grab yours today.
How much does it cost to rent a holiday home in Chesterfield?
Property type, length of stay and time of year are some things that can influence the price of a holiday home. Simply click on your travel dates to find your ideal fit. From quaint country cottages to sprawling villas, all Bookabach holiday homes provide amazing value.
How much does it cost to rent a beach house in Chesterfield?
When you travel and the size and style of the property will determine the cost of your beachside escape. Click on your Chesterfield travel dates to see your options on Bookabach. Can't live without a hot tub? Use the filters to pick the features and amenities you want in your beach house.
Are there pet-friendly holiday homes in Chesterfield?
Pack a travel bag for your pooch because Chesterfield has eight holiday homes that throw out the welcome mat to pets. Let your happy hound enjoy the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Chesterfield?
Dig out your swimwear and inflatable unicorn, because there are three houses with a private pool in Chesterfield. Unwind at one of these terrific holiday homes and every day can be a pool day. Simply enter your dates into Bookabach, then check the "pool" filter to find the ideal place for a splashing good time!
What are popular home amenities in Chesterfield?
A barbecue grill, a garden and a swimming pool top the list of most popular home amenities in Chesterfield. Whether you're travelling alone, with your better half or a group of friends, Bookabach can help you find a holiday home that suits your style with all the features you're looking for.
Are there large group holiday homes in Chesterfield?
With four Chesterfield properties that can accommodate five or more people, you can bring a few extra family members or pals along. Whether you're planning a casual get-together or a special celebration, we'll help you book a comfortable space to fit the occasion.
Are there holiday homes in Chesterfield that welcome kids?
With eight family-friendly holiday homes available in Chesterfield, there's never been a better time to introduce the kiddos to the pleasures of travel. Simply check our "Properties good for families" filter to look for stays that come with amenities perfect for families on the move, like full kitchens, swimming pools, bunk beds and entertainment areas.
What are the top attractions for families in Chesterfield?
You'll find lots of cool things to see and do with the family in Chesterfield, such as:

  • Chesterfield Sports Fusion
  • Museum of Transportation
  • Kokomo Joes Family Fun Centre

Are there one-bedroom holiday homes in Chesterfield?
You'll find three one-bedroom properties in Chesterfield to pick from. A one-bedroom holiday home is an excellent choice if it's only the two of you or if you're holidaying solo. Add in more convenience, privacy and space compared to a regular hotel, and you'll be sure to have a trip to remember.
Can I find two-bedroom holiday homes in Chesterfield?
Choose from five two-bedroom homes in Chesterfield. Put your little ones in the second room or fill it with a couple of your best buddies. There's ample space for whoever's fortunate enough to be joining in on the fun.
How can I find holiday homes with air conditioning in Chesterfield?
Chesterfield has eight holiday homes where you can unwind in air-conditioned comfort. To book a stay on Bookabach that has this perk, enter your preferred travel dates and use the filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Chesterfield?
The minimum required age is typically 16, 18 or 21. It can change across properties on Bookabach, so check the rules of your preferred Chesterfield holiday home before making a booking.
How long can I rent a holiday home in Chesterfield for?
The amount of time you can book a Chesterfield holiday home for depends on the property. Simply enter your travel dates to browse available options that offer extended stays. They come with everything you need to make your extended getaway more convenient and comfortable, like laundries and air conditioning. Some Bookabach holiday properties may also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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