Chesterfield holiday lettings

We found 1,680 holiday rentals — enter your dates for availability

Discover a selection of 12 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:10 Jul - 17 Jul

Image gallery for Bellsworth Bungalow

Living area
9.0 out of 10, Wonderful, (14 reviews)
Wonderful
(14 reviews)

Bellsworth Bungalow

St. Louis

7% off
Price is £624
for 7 nights, 1 home
£89 per night
includes taxes & fees
Bellsworth Bungalow

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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:

  • St. Louis Zoo (14.9 mi / 24 km)
  • Bellerive Country Club (4.4 mi / 7.1 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)

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 best area to stay in Chesterfield when booking a holiday rental?
When considering a holiday rental in Chesterfield, Missouri, a popular area to stay is near the vibrant Town and Country neighbourhood. This area boasts a delightful mix of upscale shopping and dining options, making it superb for those who enjoy a bit of retail therapy. You can explore the nearby Chesterfield Mall, which features a variety of stores and eateries, offering something for everyone.

Another excellent choice would be the Chesterfield Valley area, known for its scenic landscapes and recreational opportunities. Here, you can enjoy the picturesque trails at the Chesterfield Valley Athletic Complex or visit the expansive Central Park, which hosts various events throughout the year and offers lovely picnic spots.

In terms of holiday rentals, Chesterfield has a diverse range of properties, from charming townhouses to spacious family homes, suiting different preferences and group sizes. Each neighbourhood provides a special environment, allowing visitors to experience the local culture while enjoying convenient access to attractions and amenities.
How much does it cost to rent a holiday home in Chesterfield?
Prices for holiday rentals in Chesterfield 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 Chesterfield 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 Chesterfield holiday house rentals?
You can find great discounts on house rentals in Chesterfield 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 Chesterfield?
In Chesterfield, apartments are the most popular type of holiday rental, with about 56 available throughout the area. These apartments are typically located in convenient neighbourhoods, providing easy access to local amenities and attractions. Most units come equipped with fully fitted kitchens, comfortable living areas, and often feature balconies or patios for relaxing outdoors. For those seeking more space, there are approximately 12 holiday houses available, which usually include multiple bedrooms, larger living areas, and private outdoor spaces, making them ideal for families or groups.
Are there any family house rentals in Chesterfield?
In Chesterfield, Missouri, there are several family house rentals available, making it an excellent choice for those travelling with children. The area boasts spacious homes in neighbourhoods like Longview Farm Park, where families can enjoy amenities such as large backyards, fully equipped kitchens for preparing family meals, and comfortable living spaces ideal for relaxation after a day of exploring.

Visitors will appreciate the proximity to local attractions, including the popular Chesterfield Mall for shopping and dining, as well as the scenic trails and playgrounds at nearby parks. Additionally, families can take advantage of nearby recreational facilities offering sports fields and picnic areas, ensuring ample opportunities for outdoor fun.
Can I find long-stay holiday rentals in Chesterfield?
A long-stay holiday rental in Chesterfield 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 Chesterfield?
In Chesterfield, there are several pet-friendly house rentals available, making it a suitable destination for travellers with furry companions. Many of these properties feature spacious layouts, fully equipped kitchens, and outdoor areas such as patios or gardens where pets can enjoy the fresh air. The neighbourhood offers a suburban atmosphere with easy access to local parks and green spaces, providing ample opportunities for pet walks and playtime. Additionally, the area is known for its family-friendly amenities, including nearby shops and restaurants that may also welcome pets.
Are there any remote work holiday rentals in Chesterfield?
In Chesterfield, Missouri, there are numerous holiday rentals suitable for remote work, with around 56 options available. Many of these properties provide essential amenities for a productive stay, including dedicated workspaces, high-speed Wi-Fi, and reliable internet access.

Travellers can expect a variety of accommodations, from modern apartments to spacious homes, often featuring comfortable living areas and well-equipped kitchens. The proximity to local parks and recreational areas offers opportunities for breaks and relaxation, making it an ideal base for those blending work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chesterfield holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chesterfield 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 Chesterfield?
In Chesterfield, popular rental amenities include well-equipped kitchens, allowing guests the convenience of preparing their own meals. Many rentals also feature dining areas for enjoying meals together, as well as comfortable desks ideal for those needing to work or study during their stay. Many properties offer balconies, providing a lovely spot to relax and take in the surrounding views. Additionally, fitness facilities are available in several rentals, suiting guests who wish to maintain their exercise routines while away.
When is the best time to visit Chesterfield for a holiday rental?
The peak season for visiting Chesterfield, Missouri, runs from May to July, with July being the most popular month for holiday rentals. During this time, visitors flock to the area to enjoy the vibrant outdoor activities and events, making it an ideal choice for those seeking a lively option. The warm weather, with temperatures averaging between 20 to 30 degrees Celsius, creates great conditions for exploring local parks, hiking trails, and nearby attractions.

If you're keen on enjoying Chesterfield's outdoor offerings, including its beautiful parks and shopping districts, visiting in June can provide a great balance of pleasant weather and a bustling community vibe. However, for those looking for a quieter experience, November presents a wonderful opportunity. This low season offers a peaceful retreat, allowing you to explore the scenic beauty of Chesterfield without the crowds. Plus, the cooler temperatures in November can be quite refreshing, making it a wonderful time for leisurely walks and enjoying the autumn colours.

Ultimately, the best time to book a holiday rental in Chesterfield will depend on your personal preferences for activity levels and comfort.
How early should I book a Chesterfield holiday rental?
Book your Chesterfield 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.
What are the top attractions in Chesterfield?
In Chesterfield, visitors can enjoy a variety of attractions that highlight the area's natural beauty and family-friendly activities. The Chesterfield Mall offers a wide range of shopping options, dining establishments, and entertainment, making it a popular destination for both locals and tourists. Nearby, the Chesterfield Valley Athletic Complex provides ample opportunities for sports enthusiasts, featuring fields for soccer, baseball, and other recreational activities.

For those who appreciate the outdoors, the scenic Butterfly House is a must-visit, showcasing a diverse array of butterflies and offering educational experiences about these beautiful creatures. The area is also home to several parks, such as Faust Park, which boasts walking trails, picnic areas, and a historic carousel, allowing families to enjoy a day of relaxation and fun.

In addition, the nearby Longview Farm Park offers picturesque landscapes and walking paths, great for leisurely strolls or family outings.
Can I change or cancel my Chesterfield home rental booking on Vrbo?
To find Chesterfield 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 Chesterfield 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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