Crestwood Vacations from $730
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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.
Louisville Marriott Downtown
Downtown Louisville
$1,205
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Property was nice! Room was as expected! Valet/service was much to be desired! Room service snd bar service was some of the worst I’ve ever encountered! Was told by room service they had water; but if I wanted then I had to come get them myself! She wasn’t delivering them! Bartender in the hotel lounge was so bad it was laughable!! Told us she was doing us a favor by waiting on us! Lost her mind when I ask for 3 small bowls to put nuts in so our party of eight didn’t have to pass around the same cardboard cup she put them in!
Reviewed on Aug 16, 2026
Stay near popular Crestwood attractions
Yew Dell Botanical Gardens
6.8/10 (3 reviews)
This historic botanical garden showcases Theodore Klein's horticultural legacy with diverse themed gardens and a distinctive stone castle. Wander through the Asian Garden for a serene escape into botanical excellence.
Kentucky Artisan Distillery
At Kentucky Artisan Distillery, witness the intimate craft of bourbon-making with hands-on access to production areas. Converse with distillers and sample spirits at their custom bar.
Summer Field by the Lake
This tranquil neighborhood park in Crestwood offers green spaces perfect for leisurely walks and picnics. Bring a blanket to enjoy the serene lakeside setting where locals gather for peaceful afternoon retreats.
Maples Park
This 22-acre community sanctuary offers peaceful walking trails and a historic limestone tea house amid lush greenery. Families particularly enjoy the modern playground and refreshing splash pad during summer visits.
Veterans Memorial Park
The Veterans Memorial Park of Kentucky honors military sacrifice with a historical walkway chronicling 300 years of service. Visitors can reflect while exploring monuments in this educational space.
South Oldham Library
This welcoming community library offers diverse books, digital resources, and educational programs for all ages. Explore year-round events or enjoy a quiet reading space in this local knowledge hub.
Peggy Baker Park
This 25-acre community hub features multiple baseball fields where the South Oldham Little League plays. Enjoy the playground, basketball court, or stroll the paved walking trail with your dog.
Oldham County Arts Center
Enjoy an outing to Oldham County Arts Center during your stay in Crestwood.
What to do in Crestwood
Kentucky Derby Museum - General Admission and Guided Track Visit
$25
per adult
92% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
$129
per adult
94% of travellers recommend
Kentucky Derby Museum - Admission with Guided Track Visit
$25
per adult
88% of travellers recommend
Crestwood Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$143 nightly
$168 total
Sep 8 - Sep 9
Total with taxes and fees
9/10 Wonderful! (4,250 reviews)
"Fantastic hotel everything you need and the area around is great for touring bourbon distilleries"
Reviewed on Aug 26, 2026
Omni Louisville Hotel
400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
$199 nightly
$234 total
Aug 30 - Aug 31
Total with taxes and fees
9.4/10 Exceptional! (2,088 reviews)
"Really enjoyed this hotel, feels very luxurious inside. Room had a bit of wear and tear but nothing crazy. Area is ok, kind of nothing around."
Reviewed on Aug 26, 2026
Holiday Inn Express & Suites Louisville Downtown by IHG
800 W Market St Louisville KY
Fully refundableReserve now, pay when you stay
$78 nightly
$92 total
Aug 27 - Aug 28
Total with taxes and fees
8.8/10 Excellent! (1,770 reviews)
"The room was clean but the staff barely acknowledged"
Reviewed on Aug 26, 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.
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 $730 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
