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

Our pick of the best Chesterfield Hotel Deals

Sonesta ES Suites St. Louis - Chesterfield
Sonesta ES Suites St. Louis - Chesterfield
3 out of 5
15431 Conway Rd, Chesterfield, MO
Stay at this hotel in Chesterfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8/10 Very Good! (1,001 reviews)
"I liked having a 2 bedroom suite with 2 bathrooms. The kitchen area was good but no coffee in the suite."

Reviewed on 26 Jun 2025

Sonesta ES Suites St. Louis - Chesterfield
Hyatt Place St. Louis/Chesterfield
Hyatt Place St. Louis/Chesterfield
3 out of 5
333 Chesterfield Center East, Chesterfield, MO
Stay at this 3-star business-friendly hotel in Chesterfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,001 reviews)
Long weekend in St Louis/Chesterfield
"Our stay was wonderful. We were in town to celebrate a family members accomplishments that lives nearby. We picked the perfect place. Great, newer, clean comfortable hotel. Friendly staff, indoor pool, fitness center, free breakfast, free covered underground parking, great location near shopping, ..."

Reviewed on 26 Jun 2025

Hyatt Place St. Louis/Chesterfield
Hyatt Regency St. Louis at The Arch
Hyatt Regency St. Louis at The Arch
4 out of 5
315 Chestnut St, St. Louis, MO
Stay at this 4-star business-friendly hotel in St. Louis. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (3,793 reviews)
"Very clean"

Reviewed on 27 Jun 2025

Hyatt Regency St. Louis at The Arch
See all 2,080 properties in Chesterfield
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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.

Discover the most popular places to visit in Chesterfield

Gateway Arch showing a city, city views and skyline

Gateway Arch

5/5(16 reviews)

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch

Dome at America’s Center

5/5(4 reviews)

Catch an event at Dome at America’s Center during your trip to St. Louis. Experience the area's fascinating museums and acclaimed art galleries.

Dome at America’s Center

Six Flags St. Louis

5/5(1 review)

Bring the children to Six Flags St. Louis and have a fun-filled day at this theme park in St. Louis. While in this romantic area, you can savour the top-notch restaurants.

Six Flags St. Louis

Unmissable things to do in Chesterfield

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

£16
per adult
94% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

£18
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
St Louis Self-Guided Driving and Walking Audio Tour

St Louis Self-Guided Driving and Walking Audio Tour

£13
per traveller
St Louis Self-Guided Driving and Walking Audio Tour
See all activities in Chesterfield

* 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.