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
Price was CA $1,558, price is now CA $1,026 per person
CA $1,026
per person
Aug 13 - Aug 17
found 18 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to St. Louis (STL)
9.2/10 Wonderful! (1,663 reviews)
Very clean & pleasant staff. Breakfast had a very good selection even though they say it is Continental style.
Reviewed on Jun 24, 2026
Ameristar Casino Resort and Spa
Price was CA $1,827, price is now CA $1,553 per person
CA $1,553
per person
Jul 29 - Aug 4
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
The spa was PHENOMENAL. Casino was just a casino…smoking and gross. Rooms were clean and staff was great.
Reviewed on Jun 23, 2026
Hilton Pennywell St. Louis at the Arch
Downtown St. Louis
Price was CA $1,987, price is now CA $1,701 per person
CA $1,701
per person
Jul 29 - Aug 4
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,088 reviews)
It was a nic hotel. Room was very clean and everything in order. The guys that checked us in was awesome
Reviewed on Jun 26, 2026
Forest Park Hotel by MDR
The Hill
Price was CA $1,269, price is now CA $1,088 per person
CA $1,088
per person
Jul 29 - Aug 4
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
7.4/10 Good! (1,601 reviews)
Tony at the front desk is a great customer service representative. Made the stay great. Thank you Tony!
Reviewed on Jun 25, 2026
Moonrise Hotel
Delmar Loop
Price was CA $1,320, price is now CA $1,076 per person
CA $1,076
per person
Aug 13 - Aug 17
found 18 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to St. Louis (STL)
9/10 Wonderful! (1,981 reviews)
Great hotel, on the Loop, staff is always helpful. On-site parking. Nice little workout room. Restaurant. Coffee shops and food nearby.
Reviewed on Jun 25, 2026
Chesterfield Hotel Deals
Drury Plaza Hotel St. Louis Chesterfield
355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Jul 4 to Jul 5
CA $187
CA $217 total
Jul 4 - Jul 5
includes taxes & fees
9.6/10 Exceptional! (1,196 reviews)
"Great place to stay not as busy as downtown locations. Convenient parking."
Reviewed on Jun 26, 2026
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Jun 29 to Jun 30
CA $226
CA $266 total
Jun 29 - Jun 30
includes taxes & fees
8.6/10 Excellent! (4,157 reviews)
"I have stayed at this hotel many times and it’s always great. The bar/restaurant has great food and service is always good. Nice location right by Arch and a few blocks from the Cardinals baseball park. The only downside is the area around it has really struggled to come back since COVID so you have ..."
Reviewed on Jun 27, 2026
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Jul 26 to Jul 27
CA $141
CA $165 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (3,250 reviews)
"Great place. Staff was very nice and helpful. Breakfast was really good . Parking was a bit confusing at first but is great to have parking. Not free on the weekends but still good."
Reviewed on Jun 27, 2026
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
What to do in Chesterfield
St. Louis Ghost Tour: Sinister Sins & Shadows
CA $33
per adult
100% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
CA $35
per adult
84% of travellers recommend
St Louis Self-Guided Driving and Walking Audio Tour
CA $24
per traveller
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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.
