Chesterfield Holidays

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Chesterfield Holiday

Our pick of the best Chesterfield Hotel Deals

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 NZ$260 per night from 2 Aug to 3 Aug
NZ$260
2 Aug - 3 Aug
includes taxes & fees
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 NZ$310 per night from 5 Aug to 6 Aug
NZ$310
5 Aug - 6 Aug
includes taxes & fees
Hyatt Regency St. Louis at The Arch
Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay

3.5 out of 5
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
The price is NZ$195 per night from 9 Aug to 10 Aug
NZ$195
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (3,273 reviews)
"Although the hotel was nice, I didn’t realize it was downtown much less that parking was in a parking garage. It was completely on the other side, which you had to go around a couple blocks to get to it. Even thought it was attached, the elevator to the garage was out of order. So it was impossible ..."

Reviewed on 25 July 2026

Clayton Plaza Hotel & Extended Stay
See all 2,309 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.

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

Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

NZ$44
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

NZ$42
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
Downtown St. Louis Smartphone Guided Audio Walking Tour App

Downtown St. Louis Smartphone Guided Audio Walking Tour App

NZ$14
per adult
100% of travellers recommend
Downtown St. Louis Smartphone Guided Audio Walking Tour App
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield holiday package cost?
You can pick up a holiday package to this top destination on Expedia. But how much your holiday to Chesterfield costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chesterfield?
December, January and February are great times to search for cheap Chesterfield holiday packages. Travelling in less busy periods means you'll typically find reduced prices on accommodation and flights.
How many days is enough for Chesterfield?
With about 2 days, you'll have plenty of time to enjoy popular neighbourhoods such as Clarkson Valley and Winchester during your Chesterfield holiday. Be sure to also add Myseum and The Factory to your sightseeing itinerary. In the mood for more adventures? Consider exploring outside of Chesterfield on day trips and tours.
Is it worth booking a holiday package to Chesterfield?
Chesterfield has all the ingredients you need for an amazing break — golfing, nature and shopping are just the start. Whether you'd like to check out sights like The Factory and Chesterfield Sports Fusion, or venture off the beaten track, you'll have plenty to do on your Chesterfield holiday.
How to find the best Chesterfield package deals?
Begin your search for a Chesterfield package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chesterfield package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chesterfield adventure underway.
Is it cheaper to book a Chesterfield holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a customised Chesterfield holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Chesterfield?
If you've got your Chesterfield travel dates finalized, book as early as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Chesterfield?

  1. Choose your dates: What you plan to do in Chesterfield and your favourite season can help you decide when to get away.
  2. Set a budget: Consider expenses like transportation, flights and meals when calculating how much to set aside for your trip to Chesterfield. Then, choose a hotel that works with your budget, whether that's an affordable option or a high-end retreat.
  3. Decide your trip length: Think about how long you'd like to spend exploring Chesterfield. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodation: After you've settled on your travel dates and duration, book 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.