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.
Holiday Inn St. Louis Arpt West-Earth City by IHG

Holiday Inn St. Louis Arpt West-Earth City by IHG

3.5 out of 5
Price was CA $1,203, price is now CA $1,047 per person
CA $1,047
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
7.6/10 Good! (1,001 reviews)

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $1,752, price is now CA $1,227 per person
CA $1,227
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,677 reviews)
This place met all expectations! Clean, comfy and great price!

Reviewed on Oct 27, 2026

The Principal Hotel

The Principal Hotel

3.5 out of 5
Price was CA $1,428, price is now CA $1,221 per person
CA $1,221
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.6/10 Exceptional! (420 reviews)

The Cheshire

The Cheshire

4 out of 5
Price was CA $1,694, price is now CA $1,465 per person
CA $1,465
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,010 reviews)

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 $1,571, price is now CA $1,362 per person
CA $1,362
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,010 reviews)

Ready to book your vacation to Crestwood?

 

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Crestwood Hotel Deals

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 $126 per night from Nov 19 to Nov 20
CA $126
CA $150 total
Nov 19 - Nov 20
includes taxes & fees
9.4/10 Exceptional! (3,321 reviews)
"This hotel is part of Drury which I've found never to disappoint"

Reviewed on Oct 27, 2026

Pear Tree Inn St. Louis Airport
Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch

3 out of 5
2 South 4th Street St. Louis MO
The price is CA $202 per night from Nov 19 to Nov 20
CA $202
CA $236 total
Nov 19 - Nov 20
includes taxes & fees
9.6/10 Exceptional! (3,816 reviews)
"It has been several years since we have stayed here. We’ve always paid a little more, to be close to the stadium, arch. Free parking & meal/drinks was a plus. This time, parking was $40 so that increased the price overall. Soo many people waiting for the meal/drinks that we couldn't stand and wait, ..."

Reviewed on Oct 27, 2026

Drury Plaza Hotel St. Louis at the Arch
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 $175 per night from Nov 25 to Nov 26
CA $175
CA $207 total
Nov 25 - Nov 26
includes taxes & fees
8.6/10 Excellent! (4,387 reviews)
"Staff are incredibly helpful and courteous. The breakfast is amazing!"

Reviewed on Oct 27, 2026

Hyatt Regency St. Louis at The Arch
See all 1,947 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 $247
per adult
StL's Signature "Sights and Bites" - Private Tour in St. Louis
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

CA $35
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 $1,047 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.