Chesterfield Vacation Packages

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Your Chesterfield Vacation

Let our vacation packages to Chesterfield inspire your next great escape. There's a whole lot to love about this amazing city, starting with the neighborhood of Valley Park, which is great for golfing and nature. Make your trip to Chesterfield even more enjoyable by going sightseeing. St. Louis Premium Outlets, Lou Fusz Soccer Complex and Westfield Chesterfield Mall are some of the leading attractions worth exploring. Whatever your travel plans or budget, organizing a tailored Chesterfield vacation is a cinch with Expedia.

Top Chesterfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
Residence Inn by Marriott St Louis Downtown
Moonrise Hotel
The Cheshire

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Chesterfield Hotel Deals

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 CA $168 per night from Jul 5 to Jul 6
CA $168
CA $195 total
Jul 5 - Jul 6
includes taxes & fees
8/10 Very good! (1,038 reviews)
"This was the third time we stayed at the Sonesta. We enjoy staying there because it’s a convenient location and they have full kitchens for cooking."

Reviewed on Jun 23, 2026

Sonesta ES Suites St. Louis - Chesterfield
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 CA $187 per night from Jul 1 to Jul 2
CA $187
CA $217 total
Jul 1 - Jul 2
includes taxes & fees
9.6/10 Exceptional! (1,191 reviews)
"Enjoyed the stay. Lots of extra. Worth the money"

Reviewed on Jun 21, 2026

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 CA $225 per night from Jun 28 to Jun 29
CA $225
CA $265 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (4,146 reviews)
"Accommodations and customer service were excellent. No issuesl during my stay."

Reviewed on Jun 23, 2026

Hyatt Regency St. Louis at The Arch
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.