Chesterfield Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 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
    Plan, book, and manage your trip all in one place

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 S$111 per night from 3 Mar to 4 Mar
S$111
includes taxes & fees
3 Mar - 4 Mar
8.4/10 Very Good! (702 reviews)
Wonderful hotel.
"This was a wonderful Super 8 hotel. Seemed new, with colorful decor, a spacious comfortable lobby, and a good breakfast with waffles. Room was great, and no wifi password was even required! A great deal for the money."

Reviewed on 17 Feb,2025

Super 8 by Wyndham Staunton
Hampton Inn by Hilton Litchfield
Hampton Inn by Hilton Litchfield
2.5 out of 5
11 Thunderbird Circle, Litchfield, IL
Fully refundableReserve now, pay when you stay
The price is S$134 per night from 5 Mar to 6 Mar
S$134
includes taxes & fees
5 Mar - 6 Mar
8.8/10 Excellent! (559 reviews)
"Ear plugs were a great touch with the highway noise"

Reviewed on 18 Feb,2025

Hampton Inn by Hilton Litchfield
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 S$130 per night from 4 Mar to 5 Mar
S$130
includes taxes & fees
4 Mar - 5 Mar
7.8/10 Good! (288 reviews)
"It was gine"

Reviewed on 17 Feb,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.

Frequently asked questions

How much does a Chesterfield holiday package cost?
You’ll find cheap prices on Expedia for your Chesterfield break. However, a range of factors like the length of stay, hotel choice and season will determine how much your holiday to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
If you’d like to score a cheap Chesterfield holiday package, consider travelling in January, February and November. You’ll generally find better rates on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Chesterfield?
The ideal duration of your Chesterfield holiday depends on what you’d like to see and do. Usually, a handful of days to a week will give you plenty of time to tick off all the major sights and discover some hidden gems along the way.
How to find the best Chesterfield package deals?
Use Expedia’s handy filters to help you find some tempting Chesterfield package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your trip for midweek, or search for Chesterfield package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it’s typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Chesterfield holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and accommodation separately. Better still, you can customise your Chesterfield getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Chesterfield?
If you’re planning a spur-of-the-moment Chesterfield holiday, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Chesterfield?

  1. Choose when to get away: Check your schedule and get your bags packed. Your favourite time of year and the activities available will also help you decide when to escape to Chesterfield.
  2. Budget wisely: In addition to the cost of your accommodation, you’ll need to consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could arise during your trip to Chesterfield.
  3. Set the duration of your trip: Start by listing all the attractions and activities you want to experience in Chesterfield. Then, estimate how long you’ll need for each, including any travel time.
  4. Combine your airfare and accommodation: After you’ve settled on your travel dates and duration, lock in the right Chesterfield holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.