Chesterfield holiday lettings

We found 1,611 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:17 Apr - 24 Apr

Image gallery for Romantic Augusta Cottage w/ hot tub

Party lights come on at sunset and go off at midnight. You can override that.
10 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)

Romantic Augusta Cottage w/ hot tub

Augusta

8% off
Price is £1,086
for 7 nights, 1 cottage
£155 per night
includes taxes & fees
Romantic Augusta Cottage w/ hot tub

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Bellerive Country Club (4.4 mi / 7.1 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)
  • Sugar Creek Winery (13.2 mi / 21.2 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)
  • Katy Trail (10.3 mi / 16.6 km)
  • August A. Busch Memorial Conservation Area (11.1 mi / 17.8 km)
  • Lindenwood Park (15.1 mi / 24.3 km)
  • Jewel Box (15.4 mi / 24.8 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 the charming neighbourhood of Chesterfield Valley. This area is known for its vibrant shopping and dining scene, making it a delightful base for your stay. Here, you'll find a variety of properties available, suiting different tastes and budgets, ensuring a comfortable and enjoyable experience.

Chesterfield Valley is particularly attractive due to its proximity to top attractions such as the Chesterfield Mall, which boasts a wide array of shops and eateries, superb for a leisurely day of shopping. Additionally, the nearby Butterfly House offers a great experience with its beautiful gardens and diverse butterfly species, making it a lovely spot for families and nature enthusiasts alike.

Another appealing neighbourhood is the historic area of Chesterfield, where you can experience a more tranquil atmosphere while still being close to essential amenities. This area features several quaint parks and walking trails, ideal for those who enjoy outdoor activities. Staying here allows easy access to attractions such as the Faust Park, which not only offers scenic walking paths but also houses the historic Faust Park Carousel, a fun activity for visitors of all ages.
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, holiday houses are the most popular type of accommodation, with around 12 available in the area. These homes typically offer spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many of these houses are situated in quiet neighbourhoods, providing a peaceful environment while still being conveniently close to local attractions. Additionally, there are several apartments available, which offer a more compact living space and are often equipped with essential amenities like kitchens and comfortable seating areas.
Are there any family house rentals in Chesterfield?
In Chesterfield, Missouri, there are some family-friendly house rentals available, with approximately 11 options to consider. This area is well-suited for families, boasting spacious homes that often come equipped with modern kitchens for preparing meals together, comfortable living areas for relaxation, and outdoor spaces great for children to play.
Can I rent a holiday home with a pool or hot tub in Chesterfield?
In Chesterfield, Missouri, there are several holiday homes available for rent that feature pools and hot tubs. This family-friendly suburb offers a variety of accommodations in neighbourhoods such as Clarkson and Longview Farm Park, providing a peaceful retreat while remaining close to local attractions.
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, offering a variety of options for travellers with furry companions. Many of these properties feature spacious layouts, modern kitchens, and outdoor spaces where pets can enjoy the fresh air. Amenities often include fenced yards, which provide a secure area for pets to roam, as well as convenient access to nearby parks.

The area is home to several lovely parks, such as the expansive Chesterfield Central Park, which boasts walking trails, picnic areas, and open green spaces great for exercise and leisure with pets. Additionally, the nearby Faust Park offers scenic walking paths and natural beauty, making it an excellent spot for pet owners to explore.
Are there any remote work holiday rentals in Chesterfield?
In Chesterfield, Missouri, there are numerous remote work-friendly holiday rentals available, with around 14 options to choose from. These properties cater specifically to those looking to blend work and leisure, often featuring amenities such as high-speed Wi-Fi and dedicated desk spaces, allowing for a productive work environment. 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 holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals conveniently. Many rentals also offer complimentary breakfast, providing a great start to the day. Free WiFi is commonly available in the rooms, ensuring that travellers can stay connected during their stay. For added convenience, rentals often feature in-room coffee makers and dishwashers, making the experience more comfortable and home-like.
When is the best time to visit Chesterfield for a holiday rental?
The best time to visit Chesterfield for a holiday rental is during the peak season from May to July, with July being the most popular month. This vibrant period attracts travellers, eager to explore the lush parks, outdoor attractions, and the charming local shops that Chesterfield has to offer. With warm temperatures averaging in the high 20s Celsius, it's superb for enjoying the outdoors, whether you're hiking the scenic trails or picnicking in one of the lovely parks.

During this time, you can also partake in various local events and festivals, which add to the lively atmosphere. The community spirit is palpable, making it an ideal time for families and groups looking to create memorable experiences together.

For those mindful of their budget, November presents a wonderful opportunity to visit Chesterfield. This quieter month allows for a more relaxed experience, with fewer crowds and the chance to enjoy the beautiful autumn scenery as the leaves change colour, all while enjoying the comfort of a holiday rental at potentially lower rates.
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 explore several attractions that highlight the area's natural beauty and recreational opportunities. The Chesterfield Mall offers a variety of shopping options and dining experiences. Nearby, the expansive Babler State Park provides trails for hiking and opportunities for picnicking amidst scenic landscapes.
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.

More holiday ideas