Chesterfield Vacation Packages

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Top Chesterfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Comfort Suites Rolla

Comfort Suites Rolla

2.5 out of 5
Price was CA $1,297, price is now CA $1,082 per person
CA $1,082
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.8/10 Excellent! (882 reviews)
It was nice and was what I expected

Reviewed on Aug. 15, 2025

Landing Downtown St. Louis

Landing Downtown St. Louis

4 out of 5
Downtown St. Louis
Price was CA $1,931, price is now CA $1,627 per person
CA $1,627
per person
Oct 16 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8/10 Very Good! (11 reviews)
It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot.

Reviewed on Jun. 8, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was CA $2,146, price is now CA $1,840 per person
CA $1,840
per person
Oct 16 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.4/10 Very Good! (1,004 reviews)
The front desk was amazing in helping us with all of our needs, and the steak house was great

Reviewed on Aug. 30, 2025

Hermann Grain Bins BNB

Hermann Grain Bins BNB

2 out of 5
Price was CA $3,025, price is now CA $2,597 per person
CA $2,597
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
No reviews
The West End

The West End

2 out of 5
Central West End
Price was CA $1,663, price is now CA $1,429 per person
CA $1,429
per person
Oct 16 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Louis (STL)
8.4/10 Very Good! (285 reviews)
Feel like home, enjoyed my stay there.

Reviewed on Aug. 28, 2025

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Chesterfield Hotel Deals

Super 8 by Wyndham Staunton

Super 8 by Wyndham Staunton

2 out of 5
1527 Herman Rd, Staunton, IL
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Sep 21 to Sep 22
CA $99
CA $110 total
Sep 21 - Sep 22
includes taxes & fees
Super 8 by Wyndham Staunton
Hampton Inn by Hilton Litchfield

Hampton Inn by Hilton Litchfield

2.5 out of 5
11 Thunderbird Circle, Litchfield, IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Sep 7 to Sep 8
CA $162
CA $178 total
Sep 7 - Sep 8
includes taxes & fees
Hampton Inn by Hilton Litchfield
Super 8 by Wyndham Jerseyville

Super 8 by Wyndham Jerseyville

2 out of 5
1303 State Highway 109, Jerseyville, IL
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Sep 14 to Sep 15
CA $110
CA $122 total
Sep 14 - Sep 15
includes taxes & fees
Super 8 by Wyndham Jerseyville
See all 23 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.