Crestwood Vacation Packages

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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.

Top Crestwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
Price was CA $1,389, price is now CA $1,150 per person
CA $1,150
per person
Sep 30 - Oct 5
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.8/10 Excellent! (1,096 reviews)
Clean room

Reviewed on Jul 9, 2026

The Mercantile on the Katy Trail

The Mercantile on the Katy Trail

4.5 out of 5
Price was CA $1,811, price is now CA $1,424 per person
CA $1,424
per person
Sep 30 - Oct 5
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9.8/10 Exceptional! (34 reviews)
This was a really unique stay in a renovated building! Loved the modern amenities and charming decor. We were able to bring our English bulldog and enjoy many of the comforts of home. We will definitely stay again!

Reviewed on Jun 28, 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 CA $2,091, price is now CA $1,667 per person
CA $1,667
per person
Sep 30 - Oct 5
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9/10 Wonderful! (1,011 reviews)
Beautiful, clean, great pool. Parking is obnoxious and costly. All tech is outdated and slow, internet stinks. Lots of extra fees on absolutely everything for no reason, nickel and dime every detail. Locations was great for walking to lots of things, and all in-house dining was delicious!

Reviewed on Jul 9, 2026

21C Museum Hotel St Louis

21C Museum Hotel St Louis

4.5 out of 5
Downtown West
Price was CA $1,511, price is now CA $1,246 per person
CA $1,246
per person
Sep 30 - Oct 5
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9/10 Wonderful! (1,938 reviews)
We really enjoyed our stay here and would be back for sure! Property is very clean and staff is really hospitable and accommodating.

Reviewed on Jul 8, 2026

Four Seasons Hotel St Louis

Four Seasons Hotel St Louis

5 out of 5
Downtown St. Louis
Price was CA $2,648, price is now CA $2,199 per person
CA $2,199
per person
Sep 30 - Oct 5
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9.4/10 Exceptional! (1,002 reviews)
It was ok

Reviewed on Jul 3, 2026

Ready to book your vacation to Crestwood?

 

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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
The price is CA $198 per night from Jul 17 to Jul 18
CA $198
CA $233 total
Jul 17 - Jul 18
includes taxes & fees
8.6/10 Excellent! (4,203 reviews)
"Great stay with amazing view of the Arch"

Reviewed on Jul 9, 2026

Hyatt Regency St. Louis at The Arch
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
The price is CA $133 per night from Jul 12 to Jul 13
CA $133
CA $156 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (3,288 reviews)
"This place was great has great staff"

Reviewed on Jul 9, 2026

Clayton Plaza Hotel & Extended Stay
Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport

2.5 out of 5
10810 Pear Tree Ln St. Ann MO
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Aug 9 to Aug 10
CA $128
CA $150 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (3,087 reviews)
"shuttle driver was very courteous"

Reviewed on Jul 10, 2026

Pear Tree Inn St. Louis Airport
See all 1,959 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.
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What to do in Crestwood

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
The Gateway Arch National Park & Museum

StL's Signature "Sights and Bites" - Private Tour in St. Louis

CA $234
per adult
StL's Signature "Sights and Bites" - Private Tour in St. Louis
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

CA $36
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
See all activities in Crestwood

Frequently asked questions

How much does a Crestwood vacation package cost?
You can grab a vacation package to this popular destination from CA $1,150 on Expedia. But how much your vacation to Crestwood costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Crestwood?
January, February and November are the best times to search for cheap Crestwood vacation packages. Opting to travel in less busy periods means you can usually find lower prices on hotels and flights.
How many days is enough for Crestwood?
Crestwood vacations can be as short or long as you like, but to get a real feel for this place, we think 2 days is a good ballpark. This will mean you can visit top attractions like Museum of Transportation and Laumeier Sculpture Park and track down some lesser-known gems. Don't miss out on neighbourhoods such as Richmond Heights and Lemay either. If you're clever with your time, you can even schedule a day trip from Crestwood too.
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 a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Crestwood package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Crestwood escape off to a flying start.
Is it cheaper to book a Crestwood vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still get the freedom to create a personalized Crestwood vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Crestwood?
Score fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Crestwood break.
How to plan a trip to Crestwood?

  1. Choose when to go: Check your calendar and get packing. Your favourite season and the activities on offer will also help you decide when to visit Crestwood.
  2. Plan your budget wisely: In addition to the cost of your stay, you should consider other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Crestwood.
  3. Decide how long to go for: Now that you know more about Crestwood, you can figure out the ideal length of your break. Create a rough plan and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: Once you've nailed down your dates and duration, book the right Crestwood 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.