Crestwood Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Crestwood Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination
$481
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this spa hotel in Elizabeth. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Horseshoe Southern Indiana Casino and Waverly Hills Sanatorium are located nearby.
Room was clean and spacious,
Reviewed on Oct 4, 2026
Cottonwood Airport & Expo Hotel Louisville
Shively
$536
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Churchill Downs and L&N Federal Credit Union Stadium are located nearby.
Hotel Distil, Autograph Collection
Downtown Louisville
$778
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Whiskey Row and KFC Yum Center are located nearby.
Everything was great during our visit. The only tarnish was breakfast service was slow. But great location and wonderful hotel.
Reviewed on Oct 4, 2026
Louisville Marriott Downtown
Downtown Louisville
$694
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions KFC Yum Center and Whiskey Row are located nearby.
Didn’t like the many homeless people right outside on the sidewalk.
Reviewed on Oct 1, 2026
Moxy Louisville Downtown
Downtown Louisville
$622
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this family-friendly hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Whiskey Row and KFC Yum Center are located nearby.
The Brown Hotel
Downtown Louisville
$605
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this luxury hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions KFC Yum Center and Whiskey Row are located nearby.
Nice old classic hotel. Friendly staff mostly. Clean room, nice robes. Great piano player at the hotel bar/restaurant area. The "Hot Brown" was as good as advertised by locals. Ice machine on our floor not working. Make up mirror mounted very high on the bathroom wall and not height adjustable. No power outlets on one side of the bed and limited on the other. This area of town seemed to be popular with the homeless, but the hotel was secure. No free parking in this city. All street and garage spaces are pay.
Reviewed on Oct 5, 2026
Crestwood Vacation Packages
Trying to plan a way to bundle your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We're here to book everything you'll need to make your Crestwood trip one to remember. With only a few clicks, you can select the best Crestwood vacation package for you and your family. We have an amazing choice of flights and hotels, and Crestwood things to do to pull from.
Crestwood Hotel Deals
Our listings include hotels that are close to all the Crestwood points of interest, and some that are just outside the city center for a more restful retreat.
We have competitive rates on everything from family-friendly resorts that satisfy all the vacation must-haves to affordable accommodations which are great for those on looking to save. You can search all the possibilities and select the lodging that is perfect for you and your family. With AARP Travel Center's Crestwood hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.
Things to do in Crestwood
Crestwood is the ideal place when you have to get away from it all. With only around 4,847 people here, this hidden-gem is good for a quite vacation. If you are unsure where to start, head towards downtown. You'll usually find some great cafes and some stores worth exploring. The city is also noted for its burgeoning art scene and a rich past that is a beacon for history fans.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Package Your Crestwood Vacation and Save
With so much happening in Crestwood, you'll be wanting to focus on your itinerary, not devoting time to finding the hotel with the lowest rate. The AARP Travel Center Powered by Expedia® allows you to easily reserve everything you wish for, and save a little money while doing it. You can plan your entire holiday, including activities in Crestwood from only one place. The hardest packing you'll have to do is for your suitcase. Book today and save!
Top Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Book a stay at this spa hotel in Louisville. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the restaurant and the helpful staff ...
Omni Louisville Hotel
400 S. 2nd Street Louisville KY
Book a stay at this spa hotel in Louisville. Enjoy a full-service spa, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Radisson Hotel Louisville North
505 Marriott Drive Clarksville IN
Book a stay at this business-friendly hotel in Clarksville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. ...
The Brown Hotel
335 W Broadway Louisville KY
Book a stay at this luxury hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean ...
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
4520 Poplar Level Rd Louisville KY
Stay at this hotel in Louisville. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Holiday Inn Express & Suites Louisville Downtown by IHG
800 W Market St Louisville KY
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Crowne Plaza Louisville Airport Expo Ctr by IHG
830 Phillips Lane Louisville KY
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
Wingate by Wyndham Louisville Fair and Expo
3200 Kemmons Drive Louisville KY
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Embassy Suites Louisville Downtown
501 South Fourth Street Louisville KY
Stay at this hotel in Louisville. Enjoy free breakfast, a free airport shuttle, and room service. Our guests praise the breakfast and the helpful staff in our ...
Louisville Marriott Downtown
280 West Jefferson Street Louisville KY
Book a stay at this business-friendly hotel in Louisville. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise ...
Cambria Hotel Louisville Downtown-Whiskey Row
120 SOUTH FLOYD ST Louisville KY
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Homewood Suites by Hilton Louisville Downtown, KY
635 W Market St Louisville KY
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Holiday Inn Louisville Downtown by IHG
101 W. Muhammad Ali Blvd Louisville KY
Stay at this hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Derby Hotel & Suites
505 K Marriot Dr Clarksville IN
Stay at this hotel in Clarksville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Louisville Slugger Museum and Whiskey Row are located ...
Towneplace Suites By Marriott Louisville Downtown
801 WEST JEFFERSON STREET Louisville KY
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Oct 23 - Sun, Oct 25
TPA
Tampa Intl.
SDF
Louisville Intl.
$242
Roundtrip
found 4 days ago
Sat, Nov 7 - Tue, Nov 17
DAL
Love Field
SDF
Louisville Intl.
$257
Roundtrip
found 4 days ago
Tue, Nov 10 - Tue, Nov 17
DAL
Love Field
SDF
Louisville Intl.
$277
Roundtrip
found 4 days ago
Sat, Oct 31 - Mon, Nov 9
DFW
Dallas-Fort Worth Intl.
SDF
Louisville Intl.
$287
Roundtrip
found 5 days ago
Thu, Oct 22 - Sun, Nov 1
TPA
Tampa Intl.
SDF
Louisville Intl.
$340
Roundtrip
found 4 days ago
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