Chesterfield Holidays

Photo by Michelle E

Top hotels in 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 S$192 per night from 31 Jul to 1 Aug
S$192
31 Jul - 1 Aug
includes taxes & fees
9.4/10 Exceptional! (1,010 reviews)
"I had a wonderful stay at this hotel and would highly recommend it to anyone visiting the area. The cleanliness was absolutely top-notch every corner of the room and common areas was spotless and well-maintained. The staff were incredibly friendly, welcoming, and always ready to help with a smile. ..."

Reviewed on 22 Jul, 2025

Hyatt Place 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 S$137 per night from 3 Aug to 4 Aug
S$137
3 Aug - 4 Aug
includes taxes & fees
8/10 Very Good! (1,014 reviews)
"To have a full studio apartment when I come to St. Louis for my Mom in the hospital and at assisted living and at such a reasonable price is just incredible. I really am happy to find this place!"

Reviewed on 23 Jul, 2025

Sonesta ES Suites 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 S$161 per night from 22 Aug to 23 Aug
S$161
22 Aug - 23 Aug
includes taxes & fees
8.4/10 Very Good! (3,878 reviews)
"Hotel was beautiful but our fridge was broken and the shower drain did not work"

Reviewed on 22 Jul, 2025

Hyatt Regency St. Louis at The Arch
See all 2,107 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.

Popular places to visit

Forest Park which includes a pond, flowers and modern architecture

Forest Park

Nature, history and cultural institutions come together in one of the United States’ largest urban parks, which buzzes with St. Louis’ dynamic community spirit.

Forest Park

What to do in Chesterfield

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

S$29
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

S$41
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
St Louis Self-Guided Driving and Walking Audio Tour

St Louis Self-Guided Driving and Walking Audio Tour

S$22
per traveller
St Louis Self-Guided Driving and Walking Audio Tour
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. 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.