Simpsonville Vacation Packages
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Your Simpsonville Vacation
When an adventure in the city is calling, answer it with a vacation package to Simpsonville. With all your travel arrangements taken care of before you leave, all you have to do here is focus on having fun. The Outlet Shoppes of the Bluegrass, Talon Winery and Long Run Golf Course are just some of the attractions you'll want to explore during your trip to Simpsonville. Browse Expedia's wide range of travel options and start planning your dream vacation to Simpsonville today.
Top Simpsonville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Brown Hotel
Downtown Louisville
CA $923
per person
Dec 5 - Dec 7
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.4/10 Exceptional! (1,333 reviews)
Small, blurry TV. No microwave. Refrigerator didn’t work. Hot water was mild at best. Parking cost a fortune. There’s an additional tourism tax added on to the bill. The hotel restaurant/bar is insanely expensive. Very thin walls. Our room had no view - the windows overlooked an alley/roof. It’s a pretty hotel but you get way more amenities and modernity from a cheaper, newer hotel.
Reviewed on Oct 4, 2026
Hyatt Regency Louisville
Downtown Louisville
CA $1,039
per person
Dec 5 - Dec 7
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Gorgeous atrium style hotel just steps away from convention center. Lots to do and see near hotel.
Reviewed on Oct 1, 2026
Hotel Distil, Autograph Collection
Downtown Louisville
CA $1,098
per person
Dec 5 - Dec 7
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.6/10 Exceptional! (507 reviews)
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
Ready to book your vacation to Simpsonville?
Simpsonville Hotel Deals
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
CA $128
CA $151 total
Oct 12 - Oct 13
includes taxes & fees
Crowne Plaza Louisville Airport Expo Ctr by IHG
830 Phillips Lane Louisville KY
Fully refundable
CA $144
CA $169 total
Oct 25 - Oct 26
includes taxes & fees
Wingate by Wyndham Louisville Fair and Expo
3200 Kemmons Drive Louisville KY
Fully refundableReserve now, pay when you stay
CA $99
CA $117 total
Nov 4 - Nov 5
includes taxes & fees
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 Simpsonville attractions
The Outlet Shoppes of the Bluegrass
9.0/10 (69 reviews)
You can find the perfect gifts to bring home at The Outlet Shoppes of the Bluegrass during your visit to Simpsonville.
Shelby Trails Park
You can take time to visit Shelby Trails Park during your travels to Simpsonville.
Whitney M. Young, Jr. Birthplace
7.4/10 (11 reviews)
You can learn about the history of Simpsonville with a stop at Whitney M. Young, Jr. Birthplace.
What to do in Simpsonville
Louisville: 3-Hour Food and History Tour of NuLu District
CA $180
per adult
94% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
CA $28
per adult
94% 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 Simpsonville vacation package cost?
You can snap up a vacation package to this top destination from CA $923 on Expedia. But how much your vacation to Simpsonville costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Simpsonville?
If you're hoping to snag a cheap Simpsonville vacation package, consider visiting in December, January and February. You'll typically find lower prices on flights and accommodations during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Simpsonville?
Generally, a handful of days is ideal for a Simpsonville vacation. With a detailed itinerary, you can go to all the main sights including Long Run Golf Course, as well as discover some hidden treasures along the way.
Is it worth booking a vacation package to Simpsonville?
Simpsonville is a good vacation destination with attractions like The Outlet Shoppes of the Bluegrass among the many things to keep you entertained. Whether you're travelling with the family or planning a trip with friends, a Simpsonville vacation promises fun for everyone.
How to find the best Simpsonville package deals?
Finding a cheap Simpsonville package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Simpsonville package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Simpsonville vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can tailor your Simpsonville escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Simpsonville?
If you're planning a spur-of-the-moment Simpsonville vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Simpsonville?
- Choose when to go: Check your schedule and get your bags packed. Your preferred time of year and the available activities will also help you decide when to vacation in Simpsonville.
- Budget wisely: On top of the price of your stay, you should consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Simpsonville.
- Decide how long to go away for: Now that you're up to speed on Simpsonville, you can work out the right length of your break. Create a rough plan and allocate enough time to cover everything you want to see.
- Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, book the perfect Simpsonville 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.
