Crestwood Vacations from $385

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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.
Hilton Garden Inn Louisville/Northeast

Hilton Garden Inn Louisville/Northeast

3 out of 5
Price was $564, price is now $385 per person
$385
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
9/10 Wonderful! (177 reviews)
This property is excellent for its proximity to downtown Louisville and one of the best prices you can get currently. Staff were friendly and helpful.

Reviewed on Sep 12, 2025

Embassy Suites Louisville East

Embassy Suites Louisville East

3.5 out of 5
Price was $817, price is now $498 per person
$498
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
The open design and the friendly staff.

Reviewed on Sep 26, 2025

Homewood Suites by Hilton Louisville-East

Homewood Suites by Hilton Louisville-East

3 out of 5
Price was $791, price is now $536 per person
$536
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
9.6/10 Exceptional! (636 reviews)
All the amenities for a temporary home away from home

Reviewed on Sep 24, 2025

Hancock House

Hancock House

3 out of 5
Downtown Louisville
Price was $1,008, price is now $696 per person
$696
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
8.2/10 Very Good! (241 reviews)
Very nice apartment near the NuLu district. Lots of great restaurants and coffee shops. Free parking which was great too. Somewhat confusing on my credit card statement, since they charged twice for half the amount. Total was fine, but confusing.

Reviewed on Aug 23, 2025

Embassy Suites Louisville Downtown

Embassy Suites Louisville Downtown

4 out of 5
Downtown Louisville
Price was $581, price is now $424 per person
$424
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,015 reviews)
Clean hotel, amazing breakfast, staff is very friendly and area is accessible!

Reviewed on Sep 26, 2025

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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 acclaimed art 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

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

$32
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
90% 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

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street, Louisville, KY
$139 nightly
The price is $164 total per night from Oct 3 to Oct 4
$164 total
Oct 3 - Oct 4
Total with taxes and fees
8.8/10 Excellent! (3,638 reviews)
"Liked how close it was to everything. Wasn't told about getting a parking pass until we were leaving."

Reviewed on Sep 22, 2025

Galt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
$199 nightly
The price is $234 total per night from Oct 19 to Oct 20
$234 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (1,623 reviews)
"Upscale stay, beautiful property, and great location! We were able to walk to so many great restaurants and the hotel really made a great experience for our first time in Louisville. Will be returning!"

Reviewed on Sep 21, 2025

Omni Louisville Hotel
Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
4520 Poplar Level Rd, Louisville, KY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Sep 28 to Sep 29
$140 total
Sep 28 - Sep 29
Total with taxes and fees
9.4/10 Exceptional! (1,456 reviews)
rest after work
"Lots of places to eat within 10 minute drive. Hotel very clean and lots to do without leaving hotel."

Reviewed on Sep 24, 2025

Derby City Gaming & Hotel - A Churchill Downs Property
See all 2,069 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 $385 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.