Crestwood Vacations from $302

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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.
The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $408, price is now $302 per person
$302
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,006 reviews)
Fun, quirky hotel. Great free breakfast.

Reviewed on May 12, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $952, price is now $438 per person
$438
per person
Jul 2 - Jul 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,639 reviews)
Hotel was in a great location. Clean room and staff was very friendly. Nice breakfast included and in room tub was great for soaking in after a long trip

Reviewed on May 15, 2026

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Save 100% on your flight
Price was $555, price is now $399 per person
$399
per person
Jul 2 - Jul 7
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.4/10 Very Good! (819 reviews)
Great hotel. Clean and the food was good.

Reviewed on May 15, 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
Save 100% on your flight
Price was $506, price is now $367 per person
$367
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9/10 Wonderful! (1,011 reviews)
Clean rooms, great staff

Reviewed on May 12, 2026

DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Save 100% on your flight
Price was $415, price is now $304 per person
$304
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,001 reviews)
The hotel was nice staff was excellent The room I had could use an upgrade it was a bit tiered. Would stay again Paul

Reviewed on May 14, 2026

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Discover the most popular places to visit in Crestwood

Busch Stadium

Busch Stadium

4.5/5(1,487 reviews)

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's acclaimed art scene or attend a baseball game.

Busch Stadium
Union Station, St. Louis, MO

St. Louis Union Station

4/5(625 reviews)

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 great live music or attend a baseball game.

St. Louis Union Station
Gateway Arch

Gateway Arch

4.5/5(2,542 reviews)

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
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

$29
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
See all activities in Crestwood

Crestwood Hotel Deals

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
$127 nightly
The price is $149 total per night from May 25 to May 26
$149 total
May 25 - May 26
Total with taxes and fees
8.6/10 Excellent! (4,034 reviews)
Maybe it was just a rough weekend for staff, I used to work for Hyatt regency as a senior captain for banquets so I’m very familiar with how Hyatt is ran. There were only a few staff members that were helpful, professional and respectful and that happen to be the gentleman that checked me in, valet ...

Reviewed on May 14, 2026

Hyatt Regency St. Louis at The Arch
Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis

3.5 out of 5
777 Casino Center Drive Maryland Heights MO
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Jun 1 to Jun 2
$136 total
Jun 1 - Jun 2
Total with taxes and fees
8.4/10 Very Good! (2,215 reviews)
Clean Rooms excellent environment

Reviewed on May 14, 2026

Hollywood Casino & Hotel St. Louis
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

3 out of 5
1088 South Highway Drive Fenton MO
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from May 18 to May 19
$103 total
May 18 - May 19
Total with taxes and fees
8/10 Very Good! (1,275 reviews)
Room felt dirty, old bed bug shells, ac didn’t work

Reviewed on May 15, 2026

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham
See all 1,870 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 $302 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.