Crestwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Christ Medina

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.

Top Crestwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Louisville KY

Wyndham Garden Louisville KY

2.5 out of 5
Jeffersontown
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Louisville (SDF)
8/10 Very Good! (115 reviews)
I thought the breakfast would have protein options

Reviewed on Aug. 16, 2025

Holiday Inn Louisville Downtown by IHG

Holiday Inn Louisville Downtown by IHG

3 out of 5
Downtown Louisville
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Louisville (SDF)
8/10 Very Good! (613 reviews)
Parking lot is small. Clean and the staff is great. Can walk to downtown in 10 min. Good location.

Reviewed on Aug. 16, 2025

Red Roof Inn Louisville East - Hurstbourne

Red Roof Inn Louisville East - Hurstbourne

2 out of 5
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Louisville (SDF)
6.8/10 (1,002 reviews)
The area was good , restaurants and convenience stores around .

Reviewed on Jul. 20, 2025

Tru by Hilton Louisville Airport

Tru by Hilton Louisville Airport

2.5 out of 5
Fairgrounds
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Louisville (SDF)
9/10 Wonderful! (923 reviews)
Very convenient to airport for early morning flight

Reviewed on Aug. 11, 2025

Days Inn & Suites by Wyndham Louisville SW

Days Inn & Suites by Wyndham Louisville SW

2 out of 5
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Louisville (SDF)
8/10 Very Good! (415 reviews)
2nd time and same room #230, all good. I just wish free breakfast offered some meat and was offered later on weekends.

Reviewed on Jun. 13, 2025

Ready to book your vacation to Crestwood?

 

Choose your dates

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
The price is CA $189 per night from Aug 31 to Sep 1
CA $189
CA $222 total
Aug 31 - Sep 1
includes taxes & fees
8.8/10 Excellent! (3,518 reviews)
"Huge property with lots to do. Accommodating staff. The restaurant swizzle inside the hotel was beautiful and the food was excellent"

Reviewed on Aug. 15, 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
The price is CA $153 per night from Aug 24 to Aug 25
CA $153
CA $180 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (745 reviews)
"Hotel is clean, staff was great and breakfast was very good. Didn't like: room was not cleaned well - hair, stains on the floor and empty water bottles left from previous guest. Safe was locked when we checked in security asked for a couple of hours to come open it"

Reviewed on Aug. 14, 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
The price is CA $220 per night from Aug 31 to Sep 1
CA $220
CA $259 total
Aug 31 - Sep 1
includes taxes & fees
9.2/10 Wonderful! (1,554 reviews)
"Enjoyed the hotel!"

Reviewed on Aug. 12, 2025

Omni Louisville Hotel
See all 2,041 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Crestwood

Kentucky Exposition Center

Kentucky Exposition Center

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

Kentucky Exposition Center
Churchill Downs showing land animals and horse riding 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 featuring 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

CA $36
per adult
Derby City Ghosts: Louisville Hauntings Tour
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

CA $28
per adult
90% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
Louisville: NuLu District Food and History Tour

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

CA $178
per adult
80% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
See all activities in Crestwood

Frequently asked questions

How much does a Crestwood vacation package cost?
You can pick up a vacation package to this top destination from CA $1,676 on Expedia. However, how much your vacation to Crestwood costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Crestwood?
January, February and November are great times to look for cheap Crestwood vacation packages. Travelling in quieter months means you'll typically find better prices on accommodations and flights.
How many days is enough for Crestwood?
Dedicate around 2 days for your Crestwood vacation to discover everything that makes this place unique. Explore popular neighbourhoods, including Middletown and Pewee Valley. Then make a beeline for top sights such as Valhalla Golf Club and Paddock Shops. With a good itinerary, you can keep busy with room for some me-time too. Want to travel outside of Crestwood? Consider squeezing in a day trip or two.
How to find the best Crestwood package deals?
Start your search for a Crestwood package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Crestwood package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Crestwood adventure off to a flying start.
Is it cheaper to book a Crestwood vacation as a package?
You can enjoy significant savings on your next Crestwood escape by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Crestwood?
Score fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Crestwood vacation.
How to plan a trip to Crestwood?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Crestwood.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Crestwood.
  3. Determine how many days away: Start by making a list of all the activities and attractions you want to experience in Crestwood. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your airfare and accommodations: After you've nailed down your dates and duration, lock in the perfect Crestwood vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.