Chesterfield Vacation Packages
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Top Chesterfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
Price was CA $1,474, price is now CA $1,015 per person
CA $1,015
per person
Jul 31 - Aug 4
just found
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
9.2/10 Wonderful! (1,634 reviews)
Nice property in the St. Louis area! Very clean and luxurious feel to it. Very safe area as it is up in the mountains and away from the city, police department is even next door. Everything is in walking distance. Our room had a very comfortable king size bed, a couch, nice chair with foot stool, desk with computer chair, fridge and small microwave. The continental breakfast even had Jimmy Dean sausage, egg and cheese biscuits. We were only there one night so we didn't get to enjoy any of the onsite amenities. It is rated as a destination and venue for weddings, etc.
Reviewed on May 17, 2026
Super 8 by Wyndham Cuba
Price was CA $1,171, price is now CA $1,036 per person
CA $1,036
per person
Jul 29 - Aug 5
just found
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
Staff were good - fairly clean room - good nights sleep very basic breakfast but for price still a great deal and good location
Reviewed on May 12, 2026
Chesterfield Hotel Deals
Super 8 by Wyndham Staunton
1527 Herman Rd Staunton IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 24 to May 25
CA $118
CA $131 total
May 24 - May 25
includes taxes & fees
8.6/10 Excellent! (788 reviews)
"Immaculate and well cared for, friendly staff, quiet, comfortable, and the supposedly continental breakfast came with waffles. Nice!"
Reviewed on May 8, 2026
Memorable Family experiences at The Castle of Palmyra.
Palmyra IL
Hampton Inn by Hilton Litchfield
11 Thunderbird Circle Litchfield IL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Jun 2 to Jun 3
CA $148
CA $163 total
Jun 2 - Jun 3
includes taxes & fees
9/10 Wonderful! (653 reviews)
"We had an excellent day while we were in town. Easy access to local restaurants and close to the freeway. Good selection for breakfast. We could see that they were in the process of updating, which is always nice to see. Staff was very friendly and helpful. Would stay here again."
Reviewed on May 18, 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.
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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.
