Chesterfield Holidays from £877

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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.
River City Casino & Hotel

River City Casino & Hotel

4 out of 5
Price was £996, price is now £877 per person
£877
per person
20 Oct - 26 Oct
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
9/10 Wonderful! (1,330 reviews)
Property was fine although the area around the property was a bit sketchy.

Reviewed on 27 Aug 2025

Seven Gables, St. Louis West, a Tribute Portfolio Hotel

Seven Gables, St. Louis West, a Tribute Portfolio Hotel

3.5 out of 5
Clayton
Price was £1,269, price is now £1,148 per person
£1,148
per person
6 Oct - 9 Oct
found 15 hours ago
Return direct flight included
London (LON) to St. Louis (STL)
8.4/10 Very Good! (568 reviews)
Very quiet. Moved to the first floor. Room very nice. Elevator was out.

Reviewed on 7 Aug 2025

DoubleTree by Hilton St. Louis Forest Park

DoubleTree by Hilton St. Louis Forest Park

4 out of 5
Central West End
Price was £1,201, price is now £1,092 per person
£1,092
per person
6 Oct - 9 Oct
found 15 hours ago
Return direct flight included
London (LON) to St. Louis (STL)
8.2/10 Very Good! (1,000 reviews)
Parking is terrible and you shouldn’t have to pay $15 to park then charge for breakfast when your paying all that money to stay!!

Reviewed on 23 Aug 2025

The Cheshire

The Cheshire

4 out of 5
Price was £1,083, price is now £997 per person
£997
per person
6 Oct - 9 Oct
found 15 hours ago
Return direct flight included
London (LON) to St. Louis (STL)
8.6/10 Excellent! (1,007 reviews)
The Cheshire kept well from of old! We felt back in to the ages yet very 21C amenities. The location is perfect to explore St. Louis. We'd like to come back!

Reviewed on 23 Aug 2025

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 £1,210, price is now £1,123 per person
£1,123
per person
6 Oct - 9 Oct
found 15 hours ago
Return direct flight included
London (LON) to St. Louis (STL)
9/10 Wonderful! (1,005 reviews)
Clean upbeat cool vibe hotel that is centrally located and offers many fun amenities.

Reviewed on 24 Aug 2025

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

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 £112 per night from 10 Sept to 11 Sept
£112
10 Sept - 11 Sept
includes taxes & fees
9.6/10 Exceptional! (1,008 reviews)
"Amazing stay - it was perfect"

Reviewed on 24 Aug 2025

Drury Plaza Hotel St. Louis 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 £75 per night from 10 Sept to 11 Sept
£75
10 Sept - 11 Sept
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"This was our second time to stay here and it was just as great as the first time. From the time we arrived until the time we left we were well cared for and really enjoyed every aspect of our stay. Each interaction we had with the staff was very positive. They were all helpful and friendly. Breakfast ..."

Reviewed on 26 Aug 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
Fully refundableReserve now, pay when you stay
The price is £106 per night from 4 Sept to 5 Sept
£106
4 Sept - 5 Sept
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
"Really nice hotel will be back!"

Reviewed on 26 Aug 2025

Hyatt Place St. Louis/Chesterfield
See all 2,070 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

Popular places to visit

Gateway Arch showing a city, city views and skyline

Gateway Arch

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

Gateway Arch

Six Flags St. Louis

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

Six Flags St. Louis

Dome at America’s Center

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

Dome at America’s Center

What to do in Chesterfield

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

£17
per adult
96% 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

£24
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
Best of St. Louis Small Group Tour w/ Arch & River Cruise

Best of St. Louis Small Group Tour w/ Arch & River Cruise

£125
per adult
84% of travellers recommend
Best of St. Louis Small Group Tour w/ Arch & River Cruise
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.

* 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.