Crestwood Vacation Packages
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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.
Top Crestwood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pillow and Paddock B&B
CA $2,082
per person
Sep 16 - Sep 21
found 5 hours ago
Roundtrip flight included
Edmonton (YEG) to Louisville (SDF)
10/10 Exceptional! (52 reviews)
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 2025
TownePlace Suites by Marriott Louisville Airport
CA $982
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.2/10 Wonderful! (219 reviews)
Ok for business people just needing a bed to sleep, but not really a family hotel with a lot of amenities. The pool was small, dimly lit and not heated.
Reviewed on Aug 1, 2026
Ready to book your vacation to Crestwood?
Crestwood Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
CA $199
CA $234 total
Sep 8 - Sep 9
includes taxes & fees
Omni Louisville Hotel
400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
CA $166
CA $196 total
Aug 16 - Aug 17
includes taxes & fees
9.4/10 Exceptional! (2,065 reviews)
"Helpful staff. Good midweek rates . Parking across the street is 7.00"
Reviewed on Aug 14, 2026
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
CA $153
CA $179 total
Aug 16 - Aug 17
includes taxes & fees
9.4/10 Exceptional! (2,438 reviews)
"This was an excellent hotel."
Reviewed on Aug 14, 2026
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.
Stay near popular Crestwood attractions
Yew Dell Botanical Gardens
6.8/10 (3 reviews)
Explore the great outdoors at Yew Dell Botanical Gardens, a lovely green space in Crestwood. Attend a sporting event while in this romantic area or simply enjoy the top-notch restaurants.
Kentucky Artisan Distillery
You can take time to visit Kentucky Artisan Distillery during your travels to Crestwood.
Summer Field by the Lake
Explore the great outdoors at Summer Field by the Lake, a lovely green space in Crestwood.
Maples Park
After visiting Maples Park, make a plan to see the other sights and activities in Crestwood.
Veterans Memorial Park
Veterans Memorial Park is just one of the places to see in Crestwood, so why not enjoy the other things to explore during your travels?
South Oldham Library
South Oldham Library is just one of the places to see in Crestwood, so why not enjoy the other things to explore during your travels?
Peggy Baker Park
Peggy Baker Park is just one of the places to see in Crestwood, so why not enjoy the other things to explore during your travels?
Oldham County Arts Center
Enjoy an outing to Oldham County Arts Center during your stay in Crestwood.
What to do in Crestwood
Louisville: 3-Hour Food and History Tour of NuLu District
CA $181
per adult
94% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
CA $28
per adult
92% of travellers recommend
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour
CA $14
per adult
80% of travellers recommend
Frequently asked questions
How much does a Crestwood vacation package cost?
You can pick up a vacation package to this top destination from CA $957 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?
- 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.
- 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.
- 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.
- 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.
