Crestwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Christ Medina

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.
Staybridge Suites - Louisville - East by IHG

Staybridge Suites - Louisville - East by IHG

3 out of 5
Middletown
per person
Sep 17 - Sep 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8/10 Very Good! (589 reviews)
The overall cleanliness & the absolute professionalism of the staff.

Reviewed on Jun. 12, 2025

Super 8 by Wyndham Louisville/Expo Center

Super 8 by Wyndham Louisville/Expo Center

2 out of 5
Fairgrounds
per person
Sep 17 - Sep 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
7.2/10 Good! (871 reviews)
The staff was extremly friendly and helpful.

Reviewed on Jun. 25, 2025

Hilton Garden Inn Louisville Downtown

Hilton Garden Inn Louisville Downtown

3.5 out of 5
Downtown Louisville
per person
Sep 17 - Sep 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.6/10 Excellent! (1,010 reviews)
Great staff, clean property, great/convenient location within walking distance to whiskey row and other points of interest. Short and relevant review I hope.

Reviewed on Jun. 29, 2025

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

3 out of 5
per person
Sep 17 - Sep 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.8/10 Excellent! (697 reviews)
I love this property. I’ve stayed there 4-5 times now. Every time I go to Louisville it’s my spot. Only knock I have on it is the pool. I may have bad luck, but last 3 times I’ve been it’s been down.

Reviewed on Jun. 9, 2025

Wingate by Wyndham Louisville Fair and Expo

Wingate by Wyndham Louisville Fair and Expo

2.5 out of 5
Hayfield Dundee
per person
Sep 17 - Sep 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.4/10 Very Good! (1,073 reviews)
The front desk staff that worked the Friday we checked in was wonderful. He knew our girls had just played 2 softball games in the heat and allowed our girls to get in the pool to cool off. However, Saturday's worker was not as wonderful. Our girls had played multiple games on Saturday in the rain and very humid heat. They were immature kicked out of the pool. I understand there are hours but they just wanted to cool off. Our girls are 14 and 15 years old and there was an adult in the pool area. He could have been a little more accommodating!

Reviewed on Jun. 29, 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
The price is CA $182 per night from Jul 3 to Jul 4
CA $182
CA $214 total
Jul 3 - Jul 4
includes taxes & fees
8.8/10 Excellent! (3,406 reviews)
"I will always stay at this property while in Louisville!"

Reviewed on Jun. 28, 2025

Galt House Hotel Trademark Collection by Wyndham
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 $267 per night from Jul 5 to Jul 6
CA $267
CA $314 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,494 reviews)
"The hotel itself and the rooms are extremely beautiful and clean. However, outside is full of homeless people. Some are mentally ill and others are drug addicts and highly aggressive."

Reviewed on Jun. 24, 2025

Omni Louisville Hotel
Radisson Hotel Louisville North
Radisson Hotel Louisville North
3 out of 5
505 Marriott Drive, Clarksville, IN
Fully refundable
The price is CA $91 per night from Jul 31 to Aug 1
CA $91
CA $103 total
Jul 31 - Aug 1
includes taxes & fees
6.8/10 (2,164 reviews)
"The property is just old and outdated but it could be so much nicer if they just cleaned it better and stayed up on the minor repairs so they don't multiply, which they have."

Reviewed on Jun. 28, 2025

Radisson Hotel Louisville North
See all 2,037 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

Frequently asked questions

How much does a Crestwood vacation package cost?
You can pick up a vacation package to this top destination from CA $1,588 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.

Discover the most popular places to visit in Crestwood

Kentucky Exposition Center

Kentucky Exposition Center

4.5/5(14 reviews)

During your trip, find out what's happening at Kentucky Exposition Center, a top convention center in Louisville. Experience the area's acclaimed theater scene and great live music.

Kentucky Exposition Center
Churchill Downs showing land animals and horse riding as well as a small group of people

Churchill Downs

4.5/5(22 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 featuring interior views

Louisville Slugger Museum

4.5/5(18 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

Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

CA $44
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

CA $177
per adult
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

CA $89
per adult
Whispers on Whiskey Row: Murder, Crime, & Ghost Tour w/Cocktail
See all activities in Crestwood
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.