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.
Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was CA $915, price is now CA $782 per person
CA $782
per person
Sep 11 - Sep 13
found 8 hours ago
Roundtrip flight included
Detroit (DTW) to St. Louis (STL)
9/10 Wonderful! (1,976 reviews)
We had to leave for a different in the middle of the night as it was so loud at this hotel. Do not stay here. The staff was very rude and unhelpful about the noise. I have never had such a bad experience at a hotel - we were left in a lurch due to the rude staff who had no regard for guests but instead were hanging out with friends in the lobby who were also going up to the rooftop bar that was so loud we could not hear ourselves in our room. Nightmare experience.

Reviewed on Jul 5, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $1,086, price is now CA $792 per person
CA $792
per person
Sep 11 - Sep 13
found 8 hours ago
Roundtrip flight included
Detroit (DTW) 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

Landing Amazing 1bd, Yoga Studio, Gym

Landing Amazing 1bd, Yoga Studio, Gym

3 out of 5
DeBaliviere Place
Price was CA $1,317, price is now CA $1,144 per person
CA $1,144
per person
Sep 11 - Sep 13
found 8 hours ago
Roundtrip flight included
Detroit (DTW) to St. Louis (STL)
No reviews

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 1 day 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 1 day ago
Roundtrip flight included
Montreal (YUL) to St. Louis (STL)
8.6/10 Excellent! (1,011 reviews)
The pool and hot tub was very clean and so was the room! But I didn’t appreciate the housekeeping staff telling me that I needed to get out and that check out was 11:00 and they had to get room ready for next guest! I had already discussed this with check in and I was sick on top of everything! Made me feel like I wasn’t an important paying guest!

Reviewed on Jul 6, 2026

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Chesterfield Hotel Deals

Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

3 out of 5
15431 Conway Rd Chesterfield MO
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jul 19 to Jul 20
CA $155
CA $179 total
Jul 19 - Jul 20
includes taxes & fees
8/10 Very good! (1,038 reviews)
"Place was a flop house. We got to the room which stunk, the sofa couch smelled worse to the point they did not even want to pull it out. We ended up immediately leaving, and had to book a different hotel. Would not recommend to anyone. Had to fight to get my money back on the additional two nights ..."

Reviewed on Jul 6, 2026

Sonesta ES Suites St. Louis - Chesterfield
Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

3 out of 5
355 Chesterfield Ctr Chesterfield MO
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Jul 12 to Jul 13
CA $193
CA $224 total
Jul 12 - Jul 13
includes taxes & fees
9.6/10 Exceptional! (1,208 reviews)
"Just a bad weekend to book July 4 Holiday -to many kids running around hotel"

Reviewed on Jul 5, 2026

Drury Plaza Hotel St. Louis Chesterfield
Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

4 out of 5
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from Jul 17 to Jul 18
CA $234
CA $276 total
Jul 17 - Jul 18
includes taxes & fees
8.6/10 Excellent! (4,184 reviews)
"good"

Reviewed on Jul 6, 2026

Hyatt Regency St. Louis at The Arch
See all 2,298 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
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Stay near popular Chesterfield attractions

St. Louis Premium Outlets

8.8/10 (369 reviews)
You can enjoy retail therapy at St. Louis Premium Outlets during your stay in Chesterfield. Discover the top-notch restaurants and great live music in this family-friendly area.
See properties

What to do in Chesterfield

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

CA $34
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

CA $36
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
St Louis Self-Guided Driving and Walking Audio Tour

St Louis Self-Guided Driving and Walking Audio Tour

CA $24
per traveller
St Louis Self-Guided Driving and Walking Audio Tour
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from CA $782 on Expedia, you'll be pleasantly surprised at how much a vacation to Chesterfield costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chesterfield?
You can typically find lower prices and better availability in December, January and February. Take a look at our cheap Chesterfield vacation packages and you could land some great off-season discounts.
How many days is enough for Chesterfield?
Chesterfield vacations can be as short or long as you like, but to get a real feel for this destination, we'd suggest 2 days is a good ballpark. This will mean you can visit major attractions like The Factory and Chesterfield Sports Fusion as well as lesser-known spots. Don't forget to explore cool areas such as Clarkson Valley and Winchester either. If you're clever with your time, you can even schedule a day trip outside of Chesterfield too.
Is it worth booking a vacation package to Chesterfield?
Chesterfield has all the ingredients you need for an amazing break — golfing, nature and shopping are just the start. Whether you want to check out sights such as The Factory and Chesterfield Sports Fusion, or venture off the beaten track, you'll find plenty to see and do on your Chesterfield vacation.
How to find the best Chesterfield package deals?
Start your search for a Chesterfield package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Chesterfield package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chesterfield getaway off to a flying start.
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 individually. Better still, you can customize your Chesterfield trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chesterfield?
If you're considering a spur-of-the-moment Chesterfield trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Chesterfield?

  1. Choose your dates: The things you plan to do in Chesterfield and your favourite season can help you decide when to go.
  2. Set a budget: Factor in expenses such as flights, food and transportation when calculating how much to save for your trip to Chesterfield. Then, pick a property that fits your budget, whether that's a low-cost option or a more upscale retreat.
  3. Decide how long to go for: Now that you know more about Chesterfield, you can figure out the ideal length of your vacation. Put together a rough itinerary and allocate enough time to cover everything you want to see.
  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.