Crestwood Vacations from $528

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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.
Candlewood Suites Louisville North by IHG

Candlewood Suites Louisville North by IHG

2.5 out of 5
Price was $642, price is now $528 per person
$528
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
New York (LGA) to Louisville (SDF)
8.4/10 Very Good! (457 reviews)
We had a couple of room problems at check-in, but Donovan took care of us and got us an agreeable suite. The room was large, clean and well equipped with a full size refrigerator, 2 burner cook top, microwave, dish washer, coffee maker, in sink disposal and china and utensils. The bathroom was spacious and clean. Overall it was ideal for our 3 day visit.

Reviewed on May 20, 2026

TownePlace Suites by Marriott Louisville Airport

TownePlace Suites by Marriott Louisville Airport

3 out of 5
Price was $795, price is now $589 per person
$589
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
New York (LGA) to Louisville (SDF)
9.2/10 Wonderful! (210 reviews)
Beds were super comfy. Breakfast was good.

Reviewed on May 6, 2026

Holiday Inn Express Louisville Airport Expo Center by IHG

Holiday Inn Express Louisville Airport Expo Center by IHG

2.5 out of 5
Hayfield Dundee
Price was $731, price is now $593 per person
$593
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
New York (LGA) to Louisville (SDF)
8.6/10 Excellent! (1,017 reviews)
everything and everyone was great

Reviewed on May 26, 2026

The Maple Retreat at Park Mammoth

The Maple Retreat at Park Mammoth

3 out of 5
Price was $1,028, price is now $836 per person
$836
per person
Jul 2 - Jul 6
found 14 hours ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
8.8/10 Excellent! (16 reviews)
Beautiful place right by the park! the views and nature are breath taking. The cabin is beautiful and clean and services are phenomenal.

Reviewed on May 27, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was $860, price is now $710 per person
$710
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.6/10 Excellent! (1,009 reviews)
After a bad experience at another hotel, we booked rooms here. Immediately the front desk folks were absolutely AMAZING. SO kind and helpful. They got us checked in very quickly. They didn't even blink an eye about the dog with us. Our room was fantastic. The bathroom was a little small-cant close the door without stepping beside the toilet. The toile was very slow to flush- hold the handle down for a good 5-10 seconds. The whole place was very clean. I did notice cleaning staff came in the room while we were gone which im not used to, so definitely put that do not disturb sign on the door. We only had 2 hiccups during our stay and staff was VERY quick to fix these for us! The pool is great as well. Very clean. Good free breakfast too. Would definitely stay here again if we come back to town!

Reviewed on May 24, 2026

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Discover the most popular places to visit in Crestwood

Kentucky Exposition Center

Kentucky Exposition Center

4.5/5(636 reviews)

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

Kentucky Exposition Center
Churchill Downs

Churchill Downs

4.5/5(555 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

Louisville Slugger Museum

4.5/5(613 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

$25
per adult
92% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Kentucky Derby Museum - Admission with Guided Track Visit

Kentucky Derby Museum - Admission with Guided Track Visit

$25
per adult
88% of travellers recommend
Kentucky Derby Museum - Admission with Guided Track Visit
Louisville: 3-Hour Food and History Tour of NuLu District

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

$129
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
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
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $104 total per night from Jun 1 to Jun 2
$104 total
Jun 1 - Jun 2
Total with taxes and fees
8.8/10 Excellent! (1,465 reviews)
"Easier to access from. I-264 especially with I 65 shutdown."

Reviewed on May 27, 2026

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
$139 nightly
The price is $163 total per night from Jun 27 to Jun 28
$163 total
Jun 27 - Jun 28
Total with taxes and fees
9/10 Wonderful! (4,167 reviews)
"Great hotel, nice location on the water. Booked a hotel through Expedia, Expedia didn’t send over the payment so I was charged by the hotel. When the hotel refunded my money, I realized that Expedia charged me $600.52 while the hotel charged me $460.69 for the same stay. Definitely check the cost ..."

Reviewed on May 26, 2026

Galt House Hotel Trademark Collection by Wyndham
Radisson Hotel Louisville North

Radisson Hotel Louisville North

3 out of 5
505 Marriott Drive Clarksville IN
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $71 total per night from May 30 to May 31
$71 total
May 30 - May 31
Total with taxes and fees
7/10 Good! (3,104 reviews)
"Clean room"

Reviewed on May 26, 2026

Radisson Hotel Louisville North
See all 2,216 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 $528 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.