Crestwood Vacations from $374

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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
Aug 25 - Aug 30
found 5 hours ago
Roundtrip non-stop flight included
Eau Claire (EAU) to Louisville (SDF)
8.8/10 Excellent! (589 reviews)
Overall this was a wonderful hotel! I would definitely recommend and stay anytime I am in Louisville! I gave 4 stars only because we weren’t told we needed pool passes at check in. We were literally in the pool and was told we needed to leave and get the passes.

Reviewed on Jun 25, 2025

Tempo By Hilton Louisville Downtown Nulu

Tempo By Hilton Louisville Downtown Nulu

3.5 out of 5
Downtown Louisville
per person
Aug 25 - Aug 30
found 5 hours ago
Roundtrip flight included
Eau Claire (EAU) to Louisville (SDF)
9.4/10 Exceptional! (603 reviews)
Very nice location. Staff excellent

Reviewed on Jun 24, 2025

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
Downtown Louisville
per person
Aug 4 - Aug 9
found 5 hours ago
Roundtrip non-stop flight included
Eau Claire (EAU) to Louisville (SDF)
8.8/10 Excellent! (3,402 reviews)
Beautiful property!

Reviewed on Jun 25, 2025

Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

2.5 out of 5
Downtown Louisville
per person
Aug 25 - Aug 30
found 5 hours ago
Roundtrip non-stop flight included
Eau Claire (EAU) to Louisville (SDF)
8.8/10 Excellent! (1,467 reviews)
Parking garage next door but had to pay $20/day.

Reviewed on Jun 23, 2025

Caesars Southern Indiana

Caesars Southern Indiana

3.5 out of 5
per person
Sep 19 - Sep 21
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.2/10 Very Good! (1,008 reviews)
Dated room and construction made parking a challenge.

Reviewed on Jun 19, 2025

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Discover the most popular places to visit in Crestwood

Ky Derby festival balloon glow.

Kentucky Exposition Center

4.5/5(628 reviews)

During your trip, find out what's happening at Kentucky Exposition Center, a top convention center in Louisville. Experience the area's acclaimed theater scene and great live music.

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

Churchill Downs

4.5/5(551 reviews)

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

4.5/5(606 reviews)

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

$24
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
Louisville: 3-Hour Food and History Tour of NuLu District
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

$30
per traveler
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
See all activities in Crestwood

Crestwood Hotel Deals

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
$133 nightly
The price is $156 total per night from Jul 1 to Jul 2
$156 total
Jul 1 - Jul 2
Total includes taxes and fees
8.8/10 Excellent! (3,411 reviews)
"Very nice location and great hotel! Will stay again."

Reviewed on Jun 23, 2025

Galt House Hotel Trademark Collection by Wyndham
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
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $111 total per night from Jul 7 to Jul 8
$111 total
Jul 7 - Jul 8
Total includes taxes and fees
8.6/10 Excellent! (611 reviews)
"Everything was excellent will stay again 👍👍"

Reviewed on Jun 23, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Omni Louisville Hotel
Omni Louisville Hotel
4 out of 5
400 S. 2nd Street, Louisville, KY
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $218 total per night from Jul 2 to Jul 3
$218 total
Jul 2 - Jul 3
Total includes taxes and fees
9.2/10 Wonderful! (1,492 reviews)
"The hotel itself and the rooms are extremely beautiful and clean. However, outside is full of homeless people. Some are mentally ill and others are drug addicts and highly aggressive."

Reviewed on Jun 24, 2025

Omni Louisville Hotel
See all 2,026 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
Louisville Intl. Airport (SDF)
Population
4,800
Top Sights
Kentucky Artisan Distillery, Locust Grove Historic Home and Danger Run

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Frequently asked questions

How much does a Crestwood vacation package cost?
You'll find cheap prices from $374 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.