Chesterfield Vacations from ￥386,810

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The Latest Chesterfield Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott St. Louis West County

Residence Inn by Marriott St. Louis West County

3 out of 5
Price was ￥455,424, price is now ￥386,810 per person
￥386,810
per person
Aug 10 - Aug 17
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to St. Louis (STL)
9.2/10 Wonderful! (257 reviews)
This property is always clean. The staff are friendly. The breakfasts are good. The courtyard is nice to have a drink or sit around the fire pit. However, you need to know that Marriott has started charging $10 a night for parking. There’s no guard there’s no security. they even warned you that they are not responsible for your car. This property is in a business park yet they feel the need to stick it to you with $10 a night Parking.

Reviewed on Jun 29, 2026

The Cheshire

The Cheshire

4 out of 5
Price was ￥458,742, price is now ￥391,258 per person
￥391,258
per person
Aug 10 - Aug 17
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
Tracy and Roxie were very helpful. Our first room was not cool enough. The air didn’t seem to work well. They helped us to change rooms on the same floor. Perfect!

Reviewed on Jul 3, 2026

Landing Amazing 1bd, Yoga Studio, Gym

Landing Amazing 1bd, Yoga Studio, Gym

3 out of 5
DeBaliviere Place
Price was ￥499,259, price is now ￥428,806 per person
￥428,806
per person
Aug 10 - Aug 17
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to St. Louis (STL)
No reviews

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was ￥451,801, price is now ￥396,133 per person
￥396,133
per person
Aug 10 - Aug 17
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to St. Louis (STL)
9/10 Wonderful! (1,976 reviews)
This hotel was amazing, the rooms were very clean, the staff was very nice, the roof top view and restaurant was very dope, the beer cheese nachos were very good, parking was easy, most nights we parked right at the door.

Reviewed on Jul 3, 2026

The Royal Sonesta Chase Park Plaza St. Louis

The Royal Sonesta Chase Park Plaza St. Louis

4.5 out of 5
Central West End
Price was ￥489,540, price is now ￥431,066 per person
￥431,066
per person
Aug 10 - Aug 17
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to St. Louis (STL)
9/10 Wonderful! (1,007 reviews)
Very pleasant stay

Reviewed on Jul 4, 2026

Find the Best Chesterfield Vacation Packages

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 ￥13,069 per night from Jul 19 to Jul 20
￥13,069
￥14,503 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 ￥18,406 per night from Jul 12 to Jul 13
￥18,406
￥20,243 total
Jul 12 - Jul 13
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.

Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from ￥386,810 on Expedia for your Chesterfield break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
If you'd like to score a cheap Chesterfield vacation package, consider traveling in January, February and November. You'll generally find better rates on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Chesterfield?
The ideal duration of your Chesterfield vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to tick off all the major sights and discover some hidden gems along the way.
How to find the best Chesterfield package deals?
Use Expedia's handy filters to help you find some tempting Chesterfield package deals. When you begin your search, simply set your maximum budget and then order 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 off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Chesterfield vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations separately. Better still, you can customize your Chesterfield getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Chesterfield?
If you're planning a spur-of-the-moment Chesterfield vacation, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Chesterfield?

  1. Choose when to get away: Check your schedule and get your bags packed. Your favorite time of year and the activities available will also help you decide when to escape to Chesterfield.
  2. Budget wisely: In addition to the cost of your accommodations, you'll need to consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could arise during your trip to Chesterfield.
  3. Set the duration of your trip: Start by listing all the attractions and activities you want to experience in Chesterfield. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, lock in the right 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.