Crestwood Vacations from $443

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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
Price was $585, price is now $443 per person
$443
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (874 reviews)
Excellent hotel, fair price and great cooked to order breakfast! Awesome location next to airport and highway 65

Reviewed on Nov 13, 2025

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

3 out of 5
Price was $978, price is now $706 per person
$706
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
No reviews
Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $699, price is now $521 per person
$521
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,004 reviews)
Room was great, but the service by the attendant that wait on me was exceptional in what she done for me.

Reviewed on Nov 8, 2025

Hyatt House Louisville East

Hyatt House Louisville East

2 out of 5
Price was $601, price is now $472 per person
$472
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.6/10 Exceptional! (1,008 reviews)
The staff was very kind and friendly, and the rooms were very clean.

Reviewed on Nov 11, 2025

21c Museum Hotel Louisville

21c Museum Hotel Louisville

4.5 out of 5
Downtown Louisville
Price was $668, price is now $533 per person
$533
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,004 reviews)
Room comfortable and clean. Staff very helpful and friendly. Loved the art!

Reviewed on Nov 11, 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)

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

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

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

$22
per adult
90% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Derby City Ghosts: Louisville Hauntings Tour

Lace, Lunacy, and Loss: Louisville Ghost Tours

$26
per adult
Lace, Lunacy, and Loss: Louisville Ghost Tours
Kentucky Derby Museum - Admission with Guided Track Visit

Kentucky Derby Museum - Admission with Guided Track Visit

$22
per adult
100% of travellers recommend
Kentucky Derby Museum - Admission with Guided Track Visit
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 $157 total per night from Nov 25 to Nov 26
$157 total
Nov 25 - Nov 26
Total with taxes and fees
8.8/10 Excellent! (3,753 reviews)
The room was very nice the view was impeccable we could see the river the barges the buildings it was just beautiful! The staff the check desk was so kind and gracious! Really enjoyed talking with her! The hotel is just beautiful! Enjoyed our stay!

Reviewed on Nov 12, 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 refundable
$103 nightly
The price is $121 total per night from Nov 20 to Nov 21
$121 total
Nov 20 - Nov 21
Total with taxes and fees
8.8/10 Excellent! (949 reviews)
Clean nice rooms, clean lobby

Reviewed on Nov 9, 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
$199 nightly
The price is $234 total per night from Nov 26 to Nov 27
$234 total
Nov 26 - Nov 27
Total with taxes and fees
9.2/10 Wonderful! (1,669 reviews)
Gorgeous room and great service

Reviewed on Nov 8, 2025

Omni Louisville Hotel
See all 2,116 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 $443 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.