Crestwood Vacations from $612

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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.
Best Western Premier Airport/Expo Center Hotel

Best Western Premier Airport/Expo Center Hotel

3.5 out of 5
Shively
Price was $785, price is now $612 per person
$612
per person
May 7 - May 10
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.6/10 Excellent! (959 reviews)
The room was clean and staff were very friendly and helpful, but i do wish the restaurant and bar were open in the evenings.

Reviewed on Jan 5, 2026

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
Save 100% on your flight
Price was $3,990, price is now $2,888 per person
$2,888
per person
Apr 29 - May 4
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,606 reviews)
They were very accommodating. I had failed to book my room correctly and they were more than understanding and helpful with making sure we got everything squared away.

Reviewed on Feb 16, 2026

Staybridge Suites - Louisville - East by IHG

Staybridge Suites - Louisville - East by IHG

3 out of 5
Middletown
Save 100% on your flight
Price was $1,538, price is now $1,171 per person
$1,171
per person
Apr 29 - May 4
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.2/10 Very Good! (658 reviews)
Denise, the manager was great!

Reviewed on Feb 7, 2026

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was $817, price is now $644 per person
$644
per person
May 7 - May 10
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (1,005 reviews)
Very clean room, the staff was friendly as well. Looking forward to our stay again next year.

Reviewed on Feb 7, 2026

Holiday Inn Louisville Downtown by IHG

Holiday Inn Louisville Downtown by IHG

3 out of 5
Downtown Louisville
Save 100% on your flight
Price was $2,148, price is now $1,695 per person
$1,695
per person
Apr 29 - May 4
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8/10 Very Good! (726 reviews)
Our check in time was at 3:00, but when we arrived they told us our room was not ready. We didn’t get a room until 5:30, but to make up for it they upgraded our room which was much appreciated. Staff stated they only had 2 housekeepers which impacted their ability to prepare rooms for new guests. Did not receive housekeeping services throughout the stay, and had to fetch new towels etc for ourselves. The parking situation was messy as well. The room was nice and clean. We enjoyed the bar in the lobby. The bartender was very kind and even gave us recommendations for restaurants in the area.

Reviewed on Feb 15, 2026

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Discover the most popular places to visit in Crestwood

Panorama Ohio River waterway riverboats and bridges leading to heart of downtown Louisville KY

KFC Yum Center

4.5/5(423 reviews)

Catch an event at KFC Yum Center during your trip to Louisville. Stroll along the riverfront or attend a sporting event in the area.

KFC Yum Center
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 lively festivals and acclaimed art scene.

Kentucky Exposition Center
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
Louisville: NuLu District Food and History Tour

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

$129
per adult
90% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Derby City Ghosts: Louisville Hauntings Tour

Lace, Lunacy, and Loss: Louisville Ghost Tours

$32
per adult
Lace, Lunacy, and Loss: Louisville Ghost Tours
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
$156 nightly
The price is $184 total per night from Mar 19 to Mar 20
$184 total
Mar 19 - Mar 20
Total with taxes and fees
8.8/10 Excellent! (4,061 reviews)
Clean, comfortable room. Sam, the bartender at Swizzle, is excellent. However, the hotel needs much better signage to the garage.

Reviewed on Feb 9, 2026

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
$107 nightly
The price is $126 total per night from Mar 17 to Mar 18
$126 total
Mar 17 - Mar 18
Total with taxes and fees
8.8/10 Excellent! (1,152 reviews)
Todo estuvo perfecto estamos muy contentos

Reviewed on Feb 9, 2026

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 Mar 19 to Mar 20
$234 total
Mar 19 - Mar 20
Total with taxes and fees
9.2/10 Wonderful! (1,769 reviews)
All good

Reviewed on Feb 5, 2026

Omni Louisville Hotel
See all 2,166 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 $612 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.