Chesterfield holiday rentals

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.

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.

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.

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.

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 Stayz.

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.

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.

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.

Stayz 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.

Stayz offers a wide selection of holiday homes 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 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.

You can find great discounts on holiday homes in Chesterfield on Stayz, 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.

To find Chesterfield holiday rentals with free cancellation, just use Stayz'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, Stayz makes it easy to book with confidence.

A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Stayz'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.

Book your Chesterfield 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 Stayz booking and occupancy data for 2024 stays.

Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chesterfield to more spacious homes.

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.

Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.

Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.