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

The Wildwood Hotel

3.5 out of 5
Price was CA $1,026, price is now CA $850 per person
CA $850
per person
Aug 5 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,661 reviews)
Enjoyed our stay everything was adequate nothing over the top just nice with comfortable beds

Reviewed on Jul 3, 2026

Garden House Bed and Breakfast

Garden House Bed and Breakfast

2 out of 5
Price was CA $1,452, price is now CA $1,277 per person
CA $1,277
per person
Sep 7 - Sep 14
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to St. Louis (STL)
8.4/10 Very good! (43 reviews)
Chris absolutely made our stay!!!! A great place, wonderful host, breakfast was great. If we go to Hannibal again, this is absolutely the place we will stay!!!!

Reviewed on Jun 22, 2026

Best Western On The River

Best Western On The River

2.5 out of 5
Price was CA $1,557, price is now CA $1,371 per person
CA $1,371
per person
Sep 7 - Sep 14
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to St. Louis (STL)
8.6/10 Excellent! (1,011 reviews)
It was okay but really needs updating. The beds are awful. Lobby was nice . I would not stand again because $255 is to expensive

Reviewed on Jul 4, 2026

Lighthouse Inn & Suites

Lighthouse Inn & Suites

4 out of 5
Price was CA $1,945, price is now CA $1,739 per person
CA $1,739
per person
Sep 7 - Sep 14
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to St. Louis (STL)
9/10 Wonderful! (30 reviews)
The owners have really outdone themselves with the remodel of this motel! They went above and beyond for our stay for our anniversary and are the nicest people. We will definitely stay again!

Reviewed on Jun 29, 2026

Motel 6 Hannibal, MO

Motel 6 Hannibal, MO

2 out of 5
Price was CA $1,246, price is now CA $1,117 per person
CA $1,117
per person
Sep 7 - Sep 14
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to St. Louis (STL)
7.4/10 Good! (1,007 reviews)
Noisy above the room

Reviewed on Jul 4, 2026

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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 $115 per night from Jul 19 to Jul 20
CA $115
CA $128 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (801 reviews)
"it was a bit in need of a touch up. but good for the price"

Reviewed on Jul 1, 2026

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 Jul 19 to Jul 20
CA $162
CA $178 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (669 reviews)
"Very nice, quite and save place to stay. The room was clean and spacious very comfortable. And they have parking for large vehicles."

Reviewed on Jun 21, 2026

Hampton Inn by Hilton Litchfield
Memorable Family experiences at The Castle of Palmyra.

Memorable Family experiences at The Castle of Palmyra.

Palmyra IL
10/10 Exceptional! (166 reviews)
"The castle was perfect! My son was getting married and the groomsmen and their ladies all spent the weekend there. The bridal party took their wedding photos there. Amazing place! Very fun! Property is lovely!"

Reviewed on Jun 15, 2026

Get rates
Memorable Family experiences at The Castle of Palmyra.
See all 28 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
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Family Vacations
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Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from CA $850 on Expedia, you'll be thrilled with how little a vacation to Chesterfield costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chesterfield?
If you'd like to score a cheap Chesterfield vacation package, consider visiting in January, February and November. You'll usually find better prices on hotels and flights during these months — perfect for budget-conscious travellers.
How many days is enough for Chesterfield?
Generally, a handful of days is enough to tick off the main sights during your Chesterfield vacation. But if you want to have time to kick back or take day tours, think about extending your trip.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to find some of the best Chesterfield package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Chesterfield package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a customized Chesterfield vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Chesterfield?
If you're planning an impromptu Chesterfield vacation, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterfield?

  1. Choose your dates: The things you'd like to do in Chesterfield and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should factor in other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may arise during your trip to Chesterfield.
  3. Set the duration of your trip: Start by listing all the attractions you want to experience in Chesterfield. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the perfect Chesterfield vacation package for you.

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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.