Chesterfield Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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

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    Plan, book, and manage your trip all in one place

Find the Best Chesterfield Vacation Packages

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 SARĀ 511 per night from Sep 2 to Sep 3
SARĀ 511
SARĀ 592 total
2 Sep - 3 Sep
includes taxes & fees
Drury Plaza Hotel 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 SARĀ 403 per night from Sep 2 to Sep 3
SARĀ 403
SARĀ 467 total
2 Sep - 3 Sep
includes taxes & fees
8/10 Very Good! (1,047 reviews)
"The professional photography on Hotels.com really sold this property I just wish it had lived up to its appearance. These rooms are converted apartment or duplexes. The fireplaces are poorly disguised at best, the mattresses old and stained, water pressure starts out great until you actually start ..."

Reviewed on 4 August 2026

Sonesta ES Suites St. Louis - Chesterfield
Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

2.5 out of 5
11 Arnage Boulevard Chesterfield MO
Fully refundable
The price is SARĀ 428 per night from Aug 16 to Aug 17
SARĀ 428
SARĀ 498 total
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Room was clean and breakfast was great. Staff was very friendly"

Reviewed on 2 August 2026

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG
See all 2,307 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

The Factory

8.8/10 (47 reviews)
The Factory hosts a diverse range of concerts in an intimate yet spacious setting with excellent acoustics. Arrive early to explore this modern venue with comfortable seating and multiple bars before performances begin.
See properties

Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Chesterfield costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chesterfield?
You can typically find lower prices and better availability in December, January and February. Take a look at our cheap Chesterfield vacation packages and you could land some great off-season discounts.
How to find the best Chesterfield package deals?
Start your search for a Chesterfield package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Chesterfield package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chesterfield getaway off to a flying start.
Is it cheaper to book a Chesterfield vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations individually. Better still, you can customize your Chesterfield trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chesterfield?
If you're considering a spur-of-the-moment Chesterfield trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Chesterfield?

  1. Choose your dates: The things you plan to do in Chesterfield and your favorite season can help you decide when to go.
  2. Set a budget: Factor in expenses such as flights, food and transportation when calculating how much to save for your trip to Chesterfield. Then, pick a property that fits your budget, whether that's a low-cost option or a more upscale retreat.
  3. Decide how long to go for: Now that you know more about Chesterfield, you can figure out the ideal length of your vacation. Put together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, lock in the right Chesterfield vacation package for you.