Chesterfield Holidays from £900

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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.

Top Chesterfield Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was £1,042, price is now £900 per person
£900
per person
1 Oct - 6 Oct
found 24 hours ago
Return flight included
London (LON) to St. Louis (STL)
8.8/10 Excellent! (1,061 reviews)
Such a cool place! So unique and filled with amazing art. The room was clean, great walkable area and not too expensive. Hotel parking is extra, I guess I didnt read the fine print, but I was glad to have a safe lot to park my car and I could go in and out easily anytime. Will stay again!

Reviewed on 9 Jul 2026

The Cheshire

The Cheshire

4 out of 5
Price was £1,219, price is now £993 per person
£993
per person
1 Oct - 6 Oct
found 24 hours ago
Return flight included
London (LON) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
Disappointed. Stayed on a road trip from Texas to Illinois. Pool played a big part in choosing the property but was unavailable during our one night stay because they were working on the roof. Would have been nice if they offered a discounted rate because of that. Breakfast was not “English style”, just a buffet. Bathroom in room was smelly. The adjacent bar/restaurant and tavern in the hotel were enjoyable.

Reviewed on 5 Jul 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was £1,220, price is now £1,040 per person
£1,040
per person
1 Oct - 6 Oct
found 24 hours ago
Return flight included
London (LON) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Our stay was amazing.

Reviewed on 10 Jul 2026

The Royal Sonesta Chase Park Plaza St. Louis

The Royal Sonesta Chase Park Plaza St. Louis

4.5 out of 5
Central West End
Price was £1,366, price is now £1,174 per person
£1,174
per person
1 Oct - 6 Oct
found 24 hours ago
Return flight included
London (LON) to St. Louis (STL)
9/10 Wonderful! (1,011 reviews)
Our AC did not cool properly, the staff made it right by moving us into another room. Very nice hotel and the area around is safe. Restaurants at the hotel are all good. I would recommend staying there.

Reviewed on 10 Jul 2026

Landing Furnished Apartments - Central West End

Landing Furnished Apartments - Central West End

3.5 out of 5
Central West End
Price was £1,138, price is now £990 per person
£990
per person
1 Oct - 6 Oct
found 24 hours ago
Return flight included
London (LON) to St. Louis (STL)
7/10 Good! (4 reviews)
Parking was behind a large mechanical gate which did not always work. Could sometimes be noisy outside in the evening due to college clientele. Had to park on the street most of the time because of gate issues.

Reviewed on 6 Jul 2026

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

Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

3 out of 5
15431 Conway Rd Chesterfield MO
Fully refundableReserve now, pay when you stay
The price is £94 per night from 26 Jul to 27 Jul
£94
26 Jul - 27 Jul
includes taxes & fees
8/10 Very good! (1,042 reviews)
"We had a unique experience living in apartment type room having kitchen, hall and bed together. Good for going longer days. Best part was having breakfast included."

Reviewed on 10 Jul 2026

Sonesta ES Suites St. Louis - Chesterfield
Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

3 out of 5
355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
The price is £118 per night from 22 Jul to 23 Jul
£118
22 Jul - 23 Jul
includes taxes & fees
9.6/10 Exceptional! (1,216 reviews)
"We didn't like the menus for dinner, and there was never bacon for breakfast! The sausage was not tasty."

Reviewed on 10 Jul 2026

Drury Plaza Hotel 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
Fully refundableReserve now, pay when you stay
The price is £123 per night from 17 Jul to 18 Jul
£123
17 Jul - 18 Jul
includes taxes & fees
8.6/10 Excellent! (4,204 reviews)
"Great stay with amazing view of the Arch"

Reviewed on 9 Jul 2026

Hyatt Regency St. Louis at The Arch
See all 2,303 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.
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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.
See properties

What to do in Chesterfield

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

£18
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

£19
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
Downtown St. Louis Smartphone Guided Audio Walking Tour App

Downtown St. Louis Smartphone Guided Audio Walking Tour App

£6
per adult
100% of travellers recommend
Downtown St. Louis Smartphone Guided Audio Walking Tour App
See all activities in Chesterfield

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

* 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.