Chesterfield Holidays from £946
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top Chesterfield Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
£969
per person
12 Nov - 14 Nov
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
9.2/10 Wonderful! (1,657 reviews)
Very nice hotel. Only concern is the single elevator, since the front desk is on a different level than the bulk of the rooms. Makes for congestion in the morning when housecleaning staff are using it.
Reviewed on 23 Sept 2026
DoubleTree by Hilton Hotel St. Louis - Chesterfield
£977
per person
12 Nov - 14 Nov
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
We stayed at this property following a concert at The Factory. It was a very convenient location for us as we did not want to drive far after a late show. Our room was clean, comfortable and very quiet. We have a restful night and would stay again in the future.
Reviewed on 20 Sept 2026
Chesterfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top hotels in Chesterfield
Hampton Inn by Hilton Litchfield
11 Thunderbird Circle Litchfield IL
Fully refundableReserve now, pay when you stay
£84
18 Oct - 19 Oct
includes taxes & fees
Super 8 by Wyndham Staunton
1527 Herman Rd Staunton IL
Fully refundableReserve now, pay when you stay
£66
30 Sept - 1 Oct
includes taxes & fees
Carlin Villa Motel
18891 Rt 4 Old Rt 66 Carlinville IL
Fully refundableReserve now, pay when you stay
£61
4 Oct - 5 Oct
includes taxes & fees
8.4/10 Very good! (253 reviews)
"Great time"
Reviewed on 18 Sept 2026
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.
Frequently asked questions
How much does a Chesterfield travel package cost?
The most affordable Chesterfield travel package is £946, so the trip of your dreams can become a reality — without a hefty price tag. Bundle flights, hotels, car rentals and more to customize a package that matches your travelling style.
If I'm not able to travel, can I cancel my Chesterfield travel package?
Yes, it's possible to cancel your Chesterfield booking if your plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
How do I get a cheap travel package to Chesterfield?
You'll save tons of cash if you combine your hotels, flights and car rentals into a Chesterfield travel package. Sometimes cheap means fewer options. But that's not the case with Expedia. We offer over 550 partner airlines and 1,000,000 properties throughout the world, so you'll always have plenty of variety to choose from. Want to save even more? Add some interesting activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Chesterfield holidays?
Expedia has teamed up with online lender Klarna to make booking your next break easier on your budget. Paying by instalment means you can spread the costs of your next adventure, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that works with your budget. Take a look at these flexible payment options:
- Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's easy monthly instalment plans. If paying just a little each month works for you, choose this option at checkout.
- Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
- Low deposit holidays: Pressing the "book now" button is easier with this plan. Put down a small deposit on your escape and then start working on your travel itinerary.
What are the top hotels in Chesterfield?
Get your holiday off to a good start by booking a stay at Super 8 by Wyndham Staunton. It's one of most popular hotels in Chesterfield. Another welcoming option is Carlin Villa Motel.
How far in advance should I book my Chesterfield holiday?
Travellers can normally compare international fares on Expedia up to 12 months prior to departure. Booking late? With a stroke of luck, it's still possible to nab a cheaper ticket just weeks before your flight.
What does an Expedia Chesterfield travel package include?
You can select from a combination of flights, hotels and rental cars. Once you've made your booking, you can add the fun stuff like tours and experiences. Want to pick your airfare class? That's easy to do too. The choice is yours when it comes to planning your dream Chesterfield escape.
What should I know before booking a Chesterfield travel package?
So many places to venture to, so many things to see. With a package, you'll be able to tick more of them off your list. Combine your flights, rental cars and hotels and get set to save.
Can I choose my airline with a Chesterfield Expedia travel package?
Most definitely. Expedia has over 550 partner airlines to select from all over the world. With such a big range of choice, finding the perfect carrier to get you to Chesterfield won't be difficult.
* 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.
