Crestwood Vacations from $362

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Your Crestwood Vacation

Our vacation packages to Crestwood allow you to customize your own adventure. Tailor your getaway to your interests and style and make every moment count in this exciting city. You'll want to do some exploring during your trip to Crestwood. Find time for big-name attractions such as E.P. Tom Sawyer State Park, Springhurst Towne Center Shopping Center and Paddock Shops. A few clicks is all it takes to build your perfect Crestwood vacation on Expedia.

The Latest Crestwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
per person
Oct 16 - Oct 19
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Louisville (SDF)
8.8/10 Excellent! (722 reviews)
Outdoor pool was the best. My kids enjoyed. The staff at Al's? They were so nice to my kids and everyone was very pleasant

Reviewed on Aug 10, 2025

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
Downtown Louisville
Save 100% on your flight
per person
Oct 16 - Oct 19
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Louisville (SDF)
8.8/10 Excellent! (3,515 reviews)
Bed was very comfortable. Free internet. Many dining options nearby.

Reviewed on Aug 10, 2025

Embassy Suites Louisville Downtown

Embassy Suites Louisville Downtown

4 out of 5
Downtown Louisville
per person
Oct 16 - Oct 19
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Louisville (SDF)
8.8/10 Excellent! (1,007 reviews)
We didn't want to pay for parking.

Reviewed on Aug 9, 2025

Caesars Southern Indiana

Caesars Southern Indiana

3.5 out of 5
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Louisville (SDF)
8.2/10 Very Good! (1,007 reviews)
This is a nice hotel. Good value, clean with a nice staff. No luck in the casino, but the room was clean and spacious.

Reviewed on Aug 7, 2025

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
per person
Oct 16 - Oct 19
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Louisville (SDF)
8.8/10 Excellent! (1,008 reviews)
The seating and bed were not soft! The pillows weren't "pillowy" ac vent was so loud! Everything was high-end except that.

Reviewed on Aug 10, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Crestwood

Ky Derby festival balloon glow.

Kentucky Exposition Center

Learn about the events happening at Kentucky Exposition Center during your trip to Louisville. Experience the area's great live music and acclaimed art scene.

Kentucky Exposition Center
Churchill Downs showing horseriding and land animals as well as a small group of people

Churchill Downs

Find more than mint juleps to enjoy at this iconic racetrack, best known as the annual host of the Kentucky Derby.

Churchill Downs
Louisville Slugger Museum showing interior views

Louisville Slugger Museum

Baseball is part of the American fabric. See where one important tool for this sport is produced in the factory that makes ball games possible.

Louisville Slugger Museum

What to do in Crestwood

Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

$26
per adult
Derby City Ghosts: Louisville Hauntings Tour
Louisville: NuLu District Food and History Tour

Louisville: 3-Hour Food and History Tour of NuLu District

$129
per adult
80% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Whispers on Whiskey Row: Murder, Crime, & Ghost Tour

Whispers on Whiskey Row: Murder, Crime, & Ghost Tour w/Cocktail

$65
per adult
80% of travellers recommend
Whispers on Whiskey Row: Murder, Crime, & Ghost Tour w/Cocktail
See all activities in Crestwood

Crestwood Hotel Deals

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane, Louisville, KY
$111 nightly
The price is $131 total per night from Aug 24 to Aug 25
$131 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (726 reviews)
"Food was great. Quiet at night"

Reviewed on Aug 2, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street, Louisville, KY
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $151 total per night from Aug 31 to Sep 1
$151 total
Aug 31 - Sep 1
Total includes taxes and fees
8.8/10 Excellent! (3,517 reviews)
"The night view was nice"

Reviewed on Aug 5, 2025

Galt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $187 total per night from Aug 29 to Aug 30
$187 total
Aug 29 - Aug 30
Total includes taxes and fees
9.2/10 Wonderful! (1,547 reviews)
"Great hotel. Lots of food options on site. Everything is walkable. Recommend. Valet parking really only option if you plan to come and go."

Reviewed on Aug 9, 2025

Omni Louisville Hotel
See all 2,040 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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Frequently asked questions

How much does a Crestwood vacation package cost?
You'll find cheap prices from $362 on Expedia for your Crestwood getaway. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Crestwood costs.
What are the cheapest months to go to Crestwood?
If you're looking to snag a cheap Crestwood vacation package, consider visiting in November, December and January. You're likely to find lower rates on airfares and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Crestwood?
With a well-organized travel plan, you can easily visit the top Crestwood sights in a handful of days. But if you prefer to discover hidden gems or go on day tours, think about booking your Crestwood vacation for longer.
How to find the best Crestwood package deals?
Use Expedia's filters to find some of the best Crestwood package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Crestwood package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Crestwood vacation as a package?
You can enjoy significant savings on your next Crestwood getaway by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Crestwood?
If you have your Crestwood vacation dates confirmed, book as soon as you can to snap up some unbeatable deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Crestwood?

  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Crestwood.
  2. Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Crestwood.
  3. Organize your Crestwood getaway with Expedia's trip planning tool: Search for and book stays and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Crestwood together.
  4. Decide your trip length: Think about how long you'd like to spend exploring Crestwood. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Crestwood vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on the highlights of Crestwood. Find all the incredible things to do in Crestwood with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Crestwood vacation packages?
If you're like us, you love traveling the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Crestwood break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.