A group of Boy Scouts walking with American flags, a red barn, and a white fence in a park.
Photo by NPS - Photo by David Newmann
Open Photo by NPS - Photo by David Newmann

Crestwood Vacations from $452

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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.
  • A hotel with a prominent tower, a fountain in the courtyard, and a well-maintained garden.
    Dec 14 - Dec 18

    The Wildwood Hotel + Flight

    Wildwood
    4 nights
    3.5 star property
    9.2/10 - Wonderful (1,680 reviews)
    "My husband and I stayed here on our wedding night. We parked in the parking garage after checking in and were able to go right into the hallway near the elevators. The jacuzzi tub was amazing! I loved that they had towels specifically for makeup as well as a makeup wipe by the sink in the bathroom because I had forgotten to bring my own. The bed was so comfortable and you couldn’t hear other people in the hallway. The continental breakfast served what most hotels serve but everything tasted so..."
    Reviewed November 6, 2026
    Roundtrip • Los Angeles (LAX) - St. Louis (STL)
    LAX - STL • 1 stop STL - LAX • 1 stop
    $686
    $452
    per traveler
    found 1 day ago
    The Wildwood Hotel
  • A modern kitchen with dark cabinetry, a marble countertop, and a central island.
    Dec 14 - Dec 18

    Remodeled and Inviting Free EV + Flight

    Fenton
    4 nights
    2.0 star property
    9.4/10 - Exceptional (3 reviews)
    "We had a great time with my family ❤️ thank you"
    Reviewed October 12, 2026
    Roundtrip • Los Angeles (LAX) - St. Louis (STL)
    LAX - STL • 1 stop STL - LAX • 1 stop
    $924
    $669
    per traveler
    found 1 day ago
    Remodeled and Inviting Free EV
  • An indoor swimming pool with clear glass walls, metal railings, and a tiled floor.
    Jan 28 - Jan 31

    Ameristar Casino Resort and Spa + Flight

    St. Charles
    3 nights
    4.5 star property
    8.6/10 - Excellent (1,092 reviews)
    "Very nice hotel, lots of amenities, and restaurants"
    Reviewed November 6, 2026
    Roundtrip • New York (EWR) - St. Louis (STL)
    EWR - STL • Nonstop STL - EWR • Nonstop
    $802
    $662
    per traveler
    found 1 day ago
    Ameristar Casino Resort and Spa
  • A courtyard with outdoor seating, a central fountain, and a view of a tower.
    Jan 28 - Jan 31

    The Knight Center at Washington University + Flight

    St. Louis
    3 nights
    2.5 star property
    9.4/10 - Exceptional (721 reviews)
    Roundtrip • New York (EWR) - St. Louis (STL)
    EWR - STL • Nonstop STL - EWR • Nonstop
    $660
    $552
    per traveler
    found 1 day ago
    The Knight Center at Washington University
  • A hotel lobby with a reception desk, seating area, and a bookshelf filled with books.
    Dec 30 - Jan 3

    Landing Furnished Apartments near Gateway Arch + Flight

    Downtown West
    4 nights
    3.0 star property
    Roundtrip • Los Angeles (LAX) - St. Louis (STL)
    LAX - STL • Nonstop STL - LAX • 1 stop
    $1,283
    $1,081
    per traveler
    found 1 day ago
    Landing Furnished Apartments near Gateway Arch

Crestwood Hotel Deals

A spacious lobby with multiple seating areas, a central coffee table, and artwork on the walls.

Best Western St. Louis-Kirkwood Route 66

Best Western St. Louis-Kirkwood Route 66
3.5 star property
1.4 mi from Crestwood
8.2 out of 10, Very good, (1,564 reviews)
$92 nightly
The price is $108
Nov 8 - Nov 9
Total with taxes and fees
Best Western St. Louis-Kirkwood Route 66
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.
See all properties in Crestwood

Frequently Asked Questions

How much does a Crestwood vacation package cost?

You can snap up a vacation package to this destination from $452 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.