Crestwood Vacations from $280

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Your Crestwood Vacation

Book a Crestwood vacation package and prepare to experience the best of this lively city. Think about staying in the neighborhood of Soulard, which is great for distilleries and craft breweries, bars and pubs and markets. Fill your spare time with tours of Grants Farm, Magic House - St. Louis Childrens Museum and Saint Louis Galleria Mall, some of the things you just have to see during your trip to Crestwood. Don't put off your visit to this destination any longer. Your dream Crestwood vacation is a couple of clicks away with Expedia.

The Latest Crestwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Save 100% on your flight
Price was $383, price is now $280 per person
$280
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (779 reviews)
Staff was informative during check-in. Room was clean and the TV even had WELCOME with my name on it. Would stay here again.

Reviewed on Dec 22, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $712, price is now $353 per person
$353
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Clean room and easy parking.

Reviewed on Feb 2, 2026

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $495, price is now $362 per person
$362
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
The Cheshire is in a class by itself. The halls and sitting areas are so full of history and there’s an ambiance that we just love. Our suite, Treasure Island, was amazing! Large, clean, luxurious and cozy with a beautiful fireplace and large jacuzzi. We had a delicious dinner at the Basso, relaxed in the very British, cozy Fox & Hound, enjoyed a coffee at the Tudor styled Starbucks and as always, enjoyed breakfast beside the fireplace. We loved our stay!

Reviewed on Jan 28, 2026

Hotel Saint Louis, Autograph Collection

Hotel Saint Louis, Autograph Collection

4 out of 5
Downtown St. Louis
Save 100% on your flight
Price was $573, price is now $420 per person
$420
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (458 reviews)
Property and room was really nice. I will be staying here in the future

Reviewed on Nov 25, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Save 100% on your flight
Price was $534, price is now $393 per person
$393
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.4/10 Very Good! (1,006 reviews)
The room was great. I enjoyed my stay.

Reviewed on Feb 3, 2026

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Discover the most popular places to visit in Crestwood

Union Station, St. Louis, MO

St. Louis Union Station

You can learn about the local history of St. Louis when you make a stop at a well-known site like St. Louis Union Station. Experience the area's acclaimed art scene or attend a baseball game.

St. Louis Union Station
St. Louis Cardinals Baseball.

Busch Stadium

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music or attend a baseball game.

Busch Stadium
Gateway Arch showing a city, a skyscraper and skyline

Gateway Arch

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch

What to do in Crestwood

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

$32
per adult
St. Louis Ghost Tour: Sinister Sins & Shadows
St. Louis Premium Driving Tour with Boat Ride & Arch

St. Louis Premium Driving Tour with Boat Ride & Arch

$174
per adult
100% of travellers recommend
St. Louis Premium Driving Tour with Boat Ride & Arch
Best of St. Louis Small Group Tour w/ Arch & River Cruise

Best of St. Louis Small Group Tour w/ Arch & River Cruise

$169
per adult
84% of travellers recommend
Best of St. Louis Small Group Tour w/ Arch & River Cruise
See all activities in Crestwood

Crestwood Hotel Deals

21C Museum Hotel St Louis

21C Museum Hotel St Louis

4.5 out of 5
1528 Locust street St. Louis MO
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $162 total per night from Feb 12 to Feb 13
$162 total
Feb 12 - Feb 13
Total with taxes and fees
9/10 Wonderful! (1,581 reviews)
Very nice and clean

Reviewed on Jan 29, 2026

21C Museum Hotel St Louis
Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay

3.5 out of 5
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $116 total per night from Feb 8 to Feb 9
$116 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (3,081 reviews)
Lovely hotel. Great breakfast

Reviewed on Jan 29, 2026

Clayton Plaza Hotel & Extended Stay
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
$129 nightly
The price is $152 total per night from Feb 28 to Mar 1
$152 total
Feb 28 - Mar 1
Total with taxes and fees
8.4/10 Very Good! (4,017 reviews)
Nice room & friendly staff!

Reviewed on Jan 28, 2026

Hyatt Regency St. Louis at The Arch
See all 1,828 properties in Crestwood
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.

Find the Best Crestwood Vacation Packages

Crestwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
12,000
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
St. Louis Zoo, Fox Theater and Anheuser-Busch Brewery

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Frequently asked questions

How much does a Crestwood vacation package cost?
You can snap up a vacation package to this destination from $280 on Expedia. But how much your vacation to Crestwood costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Crestwood?
If you're hoping to book a cheap Crestwood vacation package, consider planning a trip in January, October and December. You're likely to find better prices on airfares and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Crestwood?
The ideal duration for your Crestwood vacation depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to go to all the top attractions and discover some hidden treasures along the way.
How to find the best Crestwood package deals?
Start your search for a Crestwood package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Crestwood package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Crestwood adventure off to a flying start.
Is it cheaper to book a Crestwood vacation as a package?
You can enjoy significant savings on your next Crestwood retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Crestwood?
If you've got your Crestwood travel dates finalized, book as early as you can to score some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Crestwood vacation packages?
Your Crestwood break should be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you that extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.