Chesterfield Holidays
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Your Chesterfield Holiday
Let our holiday packages to Chesterfield inspire your next great escape. There's a whole lot to love about this amazing city, starting with the neighbourhood of Valley Park, which is great for golfing and nature. Make your trip to Chesterfield even more enjoyable by going sightseeing. St. Louis Premium Outlets, Lou Fusz Soccer Complex and Westfield Chesterfield Mall are some of the leading attractions worth exploring. Whatever your travel plans or budget, organising a tailored Chesterfield holiday is a cinch with Expedia.
Chesterfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Lambert-St. Louis Intl. Airport (STL) |
Population | 47,900 |
Max Temp Winter | 4ºC |
Max Temp Summer | 32ºC |
Top Sights | Six Flags St. Louis, Magic House - St. Louis Childrens Museum and Route 66 State Park |
Top hotels in Chesterfield
Drury Plaza Hotel St. Louis Chesterfield
355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
£111
30 Aug - 31 Aug
includes taxes & fees
9.6/10 Exceptional! (1,259 reviews)
"Very friendly staff!"
Reviewed on 24 Aug 2026
Sonesta ES Suites St. Louis - Chesterfield
15431 Conway Rd Chesterfield MO
Fully refundableReserve now, pay when you stay
£85
25 Aug - 26 Aug
includes taxes & fees
8/10 Very good! (1,051 reviews)
"Nice"
Reviewed on 24 Aug 2026
Holiday Inn Express & Suites St. Louis - Chesterfield by IHG
11 Arnage Boulevard Chesterfield MO
Fully refundable
£97
30 Aug - 31 Aug
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Chesterfield attractions
St. Louis Premium Outlets
8.8/10 (369 reviews)
You can find the perfect gifts to bring home at St. Louis Premium Outlets during your stay in Chesterfield. Discover the top-notch restaurants and great live music in this family-friendly area.
The Factory
8.8/10 (47 reviews)
The Factory hosts a diverse range of concerts in an intimate yet spacious setting with excellent acoustics. Arrive early to explore this modern venue with comfortable seating and multiple bars before performances begin.
Babler State Park
8.6/10 (59 reviews)
This 2,500-acre natural haven offers miles of forest trails through scenic Ozark landscapes. Explore limestone valleys, spot native wildlife, and enjoy camping under the stars in Missouri's tranquil wilderness.
Sophia M. Sachs Butterfly House
8.8/10 (72 reviews)
Step into a tropical paradise where over 1,500 butterflies flutter freely through an 8,000-square-foot glass conservatory. Morning visits offer the best chance to witness these delicate creatures at their most active.
St. Louis Carousel
This century-old St. Louis Carousel features 60+ hand-carved wooden horses and deer in a climate-controlled pavilion. Enjoy nostalgic organ music while admiring the intricate craftsmanship of this rare antique treasure.
Dr. Edmund A. Babler Memorial State Park
8.2/10 (57 reviews)
You can take time to visit Dr. Edmund A. Babler Memorial State Park during your travels to Chesterfield. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Topgolf
This high-tech golf venue blends precision tracking technology with casual fun for all skill levels. Enjoy climate-controlled hitting bays while savouring chef-prepared dishes delivered to your game area.
Chesterfield Amphitheater
This modern amphitheatre hosts diverse performances with stellar acoustics in a picturesque park setting. Enjoy evening concerts under the stars from April to October, with both fixed seating and lawn spaces available.
What to do in Chesterfield
St. Louis Ghost Tour: Sinister Sins & Shadows
£18
per adult
100% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
£19
per adult
84% of travellers recommend
St. Louis & Gateway Arch NP Self Guided Drive & Walk Audio Tour
£13
per traveller
Frequently asked questions
Why should I book my Chesterfield holiday with Expedia?
With great-value flights, accommodation and car hire choices all in one place, Expedia makes booking your Chesterfield break easy. What's more, we can help you bundle your bookings into a package holiday so you can get even more savings. Pick from awesome stays, add flights and/or a hire car (and maybe also some exciting activities!) and score unbeatable prices. Need to change plans? Expedia has a flexible cancellation policy for many bookings. To learn more, visit our Customer Service Portal link.
When is the best time of year to holiday in Chesterfield?
If you'd like to experience the buzz of Chesterfield during peak season, plan your getaway for May, July and August. December, January and February are typically the quietest months of the year. Plan your visit to Chesterfield based on what kind of holiday you're looking for. January is the coolest month, when average daytime temperatures are 0ºC. In July, the warmest month, you'll experience averages of 26ºC during the day.
What is the top hotel for my holiday in Chesterfield?
Relax in comfort in Chesterfield by choosing Best Western Route 66 Rail Haven as your home base and gateway to fun and adventure.
How do I get a cheap holiday to Chesterfield?
If you love getting an amazing deal, combine your bookings into a Chesterfield holiday. Whether you're searching for hotels, flights, tours or hire cars, you can browse and book them all in one place. You'll have loads of choice at your fingertips as well. Expedia has over 400 partner airlines and 321,000 hotels worldwide to choose from. Fly with who you want, stay anywhere you like and save a tidy sum — now that's the perfect escape! Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Chesterfield holiday?
Offering major attractions like Ameristar Casino St. Charles and Westport Plaza, a holiday in Chesterfield promises plenty of exciting places to visit. Hollywood Casino Amphitheatre and St Charles Convention Centre are two other sights worth checking out.
What is the best area to stay in when on holiday in Chesterfield?
If you plan to check out St. Louis Premium Outlets, maximise your time sightseeing and lock in a stay nearby. It's one of the most popular attractions in Chesterfield.
Do I need a visa for my Chesterfield holiday?
Official government websites are the best source of information on visa requirements, application procedures and necessary documentation. Your nationality and reason for visiting, whether it be for work or holidays, will determine if you need a visa for Chesterfield. Also double-check that your passport is up to date and has a minimum of six months validity remaining after your return date. Finalise all your travel planning well ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Chesterfield holiday?
Though everyone's fashion style is different, it can help to have a few guidelines for what to bring during your holiday in Chesterfield. We recommend searching style blogs before you leave to get inspiration for local fashion trends. Be sure to check the local weather forecast so you can pack appropriately. The warmest time of year in Chesterfield is July, with average daily temperatures of 26ºC. If you plan to travel during the coolest month of January, the mercury averages 0ºC during the day.
What does an Expedia Chesterfield holiday include?
Hotels, car hires and flights, or any combination of the three — it's your choice. Whether you're visiting Chesterfield with the family or adventuring with your friends, there's a bundle to match every budget and style. Once you've made your booking, why not add on a few activities? Discover a huge range of property types and select one that suits your group size. The most sought-after holiday rentals here are private holiday homes and hotels. With Expedia, it's easy to tailor your Chesterfield retreat however you like.
Does Expedia offer Book Now, Pay Later Chesterfield holidays?
Expedia has partnered with online lender Klarna to make booking your next break a little easier on the wallet. Paying in instalments means you can spread the costs of your next big adventure, leaving you with more cash to spend while you're away. Klarna has several payment plans to pick from, so you're sure to find something that fits your budget. Consider these flexible payment options:
- Pay monthly holidays: If paying across multiple transactions is what works best for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams come true.
- No-deposit holidays: If no upfront fee for your getaway makes pressing that "book now" button easier, choose a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!
Can I choose my airline with a Chesterfield Expedia holiday?
Yes — and it's simple too. Expedia has access to more than 400 partner airlines around the world. Our holiday packages give you the flexibility to take your pick of available flights, hotels and activities that fit your needs.
Explore a world of travel with Expedia
- 5 Star Hotels in Chesterfield
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- Days Inn and Suites by Wyndham St. Louis/Westport Plaza
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- Flights to Kirkwood
- Flights to Lambert-St. Louis Intl.
- Flights to Maryland Heights
- Flights to St. Charles
- Flights to St. Louis
- Flights from Lambert-St. Louis Intl.
- British Airways London (LHR) to St. Louis (STL) flights
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- Missouri Botanical Gardens and Arboretum
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
