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Chesterfield holiday lettings

We found 1,539 holiday rentals — enter your dates for availability

Discover a selection of 13 homes, 10 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:14 Nov - 21 Nov
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Find out more about Chesterfield

Find out more about Chesterfield

Why visit Chesterfield

  • Family-friendly attractions: Chesterfield boasts a variety of activities perfect for families, ensuring everyone has a delightful time.
  • Chesterfield Town Centre: Enjoy a vibrant shopping and dining experience in the heart of the town.
  • Beautiful parks: Relax and unwind in local parks that offer scenic views and recreational opportunities.
  • Cultural experiences: Discover romantic and historical sites that enhance your visit with unique vibes.
  • Diverse accommodation options: Choose from charming holiday homes, modern apartments, and cosy guest houses for your stay.

Popular types of accommodation in Chesterfield

Planning a getaway to Chesterfield? The next exciting step is selecting your perfect home away from home. Explore a variety of accommodation options, including charming private holiday homes, modern apartments, and cosy guest houses. Whether you're seeking a stylish flat or a spacious rental, Chesterfield offers an array of holiday rentals to suit every traveller's needs. Dive into your search and discover the ideal base for your adventure!

  • Houses: The top choice for holidaymakers in Chesterfield, offering spacious and comfortable stays suited for families or groups.
  • Apartments: A popular second option, ideal for those seeking a convenient and self-contained living space during their visit.
  • Condos: A favoured third option, providing modern amenities and a community feel for an enjoyable stay.
  • Cabins: Often chosen for a rustic experience, these cosy retreats are perfect for nature lovers.
  • Cottages: Charming and quaint, cottages offer a delightful stay for those wanting a homely atmosphere.**

Top attractions near Chesterfield

Chesterfield is an ideal destination for families and those seeking entertainment or a city experience. You can explore a variety of attractions, including an arena entertainment facility, a modern college or university, and a national or state park. These points of interest provide a blend of culture and leisure, ensuring a delightful visit for all travellers.

  • Hollywood Casino Amphitheatre: An exciting venue for live performances, this amphitheatre offers a vibrant atmosphere for families and music lovers alike, located 5.0km from Chesterfield.
  • Westport Plaza: A lively neighbourhood featuring a variety of restaurants, shops, and entertainment options, creating a bustling city vibe just 4.3km from Chesterfield.
  • Washington University in St. Louis: A renowned modern university with stunning architecture and green spaces, providing a cultured city atmosphere 8.7km away from Chesterfield.

Things to do recommended for couples

Chesterfield offers delightful romantic experiences for couples. Indulge in the luxury vibes at Bellerive Country Club, embrace the thrill at Hidden Valley Ski Resort, or enjoy a charming afternoon at Chandler Hill Vineyards, where romance and entertainment await just a short drive away.

Things to do recommended for families

Families can enjoy the thrill of the Lou Fusz Soccer Complex, just 2.5km from Chesterfield, or have a blast at Chesterfield Sports Fusion, an exciting arcade adventure. For a unique experience, the Centene Community Ice Center, 5.0km away, offers ice skating fun for all ages.

Things to do recommended for groups

Groups visiting Chesterfield can indulge in retail therapy at the St. Louis Premium Outlets, enjoy a round of golf at the Missouri Bluffs Golf Course, or embark on an adventure along the scenic Katy Trail, perfect for outdoor enthusiasts.

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

If you're travelling with a group, family, or pets, or if you're considering longer stays, it's important to set your preferences accordingly. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Chesterfield with a group: Think about how many bedrooms you’ll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Chesterfield with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Chesterfield: For many families, a holiday isn’t truly fulfilling without their beloved pet. If you can relate, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels completely 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Chesterfield

Chesterfield, Missouri, offers a delightful blend of family-friendly activities and charming scenery, making it a perfect holiday destination. Explore the vibrant Chesterfield Town Centre for shopping and dining, or enjoy the local parks for a relaxing day out. Nearby, you can uncover romantic and historical vibes that add to your experience. With various holiday rentals available, your stay in the heart of Chesterfield promises to be both enjoyable and memorable.

  • St. Charles: Located approximately 6.2km from Chesterfield, St. Charles is a charming city that perfectly blends family-friendly attractions with a romantic atmosphere. Visitors can enjoy a variety of activities, including thrilling events at the arena entertainment facility and captivating performances at the local theatre. The bustling shopping mall centre offers a delightful retail experience, while nearby landmarks like the historic district and event conference venue provide a glimpse into the city’s rich heritage. St. Charles is ideal for those seeking both adventure and relaxation.
  • Clarkson Valley: Just 1.9km away from Chesterfield, Clarkson Valley is a tranquil city perfect for families and outdoor enthusiasts. The area boasts an exciting arcade adventure zone that promises fun for all ages, alongside a convenient shopping centre for a relaxed retail experience. With its inviting urban parks and a vibrant tourist precinct, Clarkson Valley offers an array of recreational activities and scenic spots for leisurely strolls. It’s a wonderful destination for those looking to enjoy the outdoors while being close to city amenities.
  • Ballwin: Situated 3.1km from Chesterfield, Ballwin is a lively city that caters to families and adventure seekers alike. The area features an exhilarating amusement park and an arcade adventure zone, making it a hit with younger visitors. Additionally, the shopping centre provides a variety of retail options for a delightful day out. Nature lovers will appreciate the proximity to national and urban parks, offering ample opportunities for hiking and outdoor exploration. Ballwin is a fantastic choice for those wanting to combine family fun with outdoor adventure.

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. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Vrbo is simple

Are you looking to cut costs on your upcoming holiday? Consider being a bit flexible with your travel dates, as prices can vary significantly. Additionally, booking an extended stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new journeys, manage your existing arrangements, or review your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover the Trip Boards, please visit: https://www.vrbo.com/en-gb/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 rental accommodation in Chesterfield?
The most in-demand types of holiday rentals in Chesterfield are houses. Looking for something different? Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo. 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 rentals in Chesterfield?
Pack a travel bag for your pooch because Chesterfield has eight holiday rentals that throw out the welcome mat to pets. Let your happy hound enjoy the family fun at one of our pet-friendly holiday rentals on Vrbo. 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 Vrbo, then check the "pool" filter to find the ideal place for a splashing good time!
What are popular rental amenities in Chesterfield?
A barbecue grill, a garden and a swimming pool top the list of most popular rental amenities in Chesterfield. Whether you're travelling alone, with your better half or a group of friends, Vrbo can help you find a holiday rental that suits your style with all the features you're looking for.
Are there large group holiday rentals 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 rentals in Chesterfield that welcome kids?
With eight family-friendly holiday rentals 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 rentals 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 rentals 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 rentals with air conditioning in Chesterfield?
Chesterfield has eight holiday rentals where you can unwind in air-conditioned comfort. To book a stay on Vrbo 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 rental in Chesterfield?
The minimum required age is typically 16, 18 or 21. It can change across properties on Vrbo, so check the rules of your preferred Chesterfield holiday home before making a booking.
How long can I rent a holiday rental 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 Vrbo holiday properties may also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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