Chesterfield Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
2ºC
Max Temp Summer
27ºC

Top hotels in Chesterfield

Super 8 by Wyndham Staunton

Super 8 by Wyndham Staunton

2 out of 5
1527 Herman Rd, Staunton, IL
Fully refundableReserve now, pay when you stay
The price is £59 per night from 3 Aug to 4 Aug
£59
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (731 reviews)
"Just stopped for the night. Nice property, clean and easy to get to. Staff was excellent!"

Reviewed on 25 Jul 2025

Super 8 by Wyndham Staunton
Memorable Family experiences at The Castle of Palmyra.

Memorable Family experiences at The Castle of Palmyra.

Palmyra, IL
9.8/10 Exceptional! (106 reviews)
"This is a great place to stay with a large family under one roof. We loved it and will come back again!"

Reviewed on 25 Jul 2025

Get rates
Memorable Family experiences at The Castle of Palmyra.
Super 8 by Wyndham Jerseyville

Super 8 by Wyndham Jerseyville

2 out of 5
1303 State Highway 109, Jerseyville, IL
Fully refundableReserve now, pay when you stay
The price is £63 per night from 17 Aug to 18 Aug
£63
17 Aug - 18 Aug
includes taxes & fees
7.8/10 Good! (305 reviews)
Great front desk!
"We stayed here while exhibiting cattle at the Jersey county fair. The front desk was very welcoming and remembered us and our dog from last year!"

Reviewed on 16 Jul 2025

Super 8 by Wyndham Jerseyville
See all 23 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

How much does a Chesterfield travel package cost?
The most affordable Chesterfield travel package is , 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.