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.
Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,273, price is now CA $1,086 per person
CA $1,086
per person
Aug 24 - Aug 28
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
8.8/10 Excellent! (1,002 reviews)

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was CA $1,503, price is now CA $1,242 per person
CA $1,242
per person
Aug 24 - Aug 28
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Everything was wonderful

Reviewed on Jul 13, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $1,336, price is now CA $1,120 per person
CA $1,120
per person
Aug 24 - Aug 28
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
8.6/10 Excellent! (1,006 reviews)

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was CA $1,841, price is now CA $1,560 per person
CA $1,560
per person
Aug 24 - Aug 28
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
9.6/10 Exceptional! (476 reviews)
The staff was their best asset! Very helpful, friendly, tried to accommodate any need!! Rooms were clean and beds were comfy!! We ate at the steakhouse in the hotel. Great food and our waitress was absolutely the best!!! The lobby could accommodate several groups of people!! Would stay there again!!

Reviewed on Jul 13, 2026

21c Museum Hotel Louisville

21c Museum Hotel Louisville

4.5 out of 5
Downtown Louisville
Price was CA $1,679, price is now CA $1,465 per person
CA $1,465
per person
Oct 9 - Oct 12
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.4/10 Exceptional! (1,000 reviews)
This unique hotel is artsy, fun, and very accommodating. Popular restaurant and bar. Art exhibits featured within the hotel are interesting, extensive, and definitely worth a look!

Reviewed on Jul 16, 2026

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Simpsonville Hotel Deals

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane Louisville KY
Fully refundable
The price is CA $135 per night from Jul 22 to Jul 23
CA $135
CA $159 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (1,718 reviews)
"Stayed here twice. Excellent!!!! 10/10"

Reviewed on Jul 15, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG
Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Jul 22 to Jul 23
CA $151
CA $177 total
Jul 22 - Jul 23
includes taxes & fees
Derby City Gaming & Hotel - A Churchill Downs Property
Wingate by Wyndham Louisville Fair and Expo

Wingate by Wyndham Louisville Fair and Expo

3 out of 5
3200 Kemmons Drive Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Aug 13 to Aug 14
CA $100
CA $117 total
Aug 13 - Aug 14
includes taxes & fees
8.4/10 Very good! (1,260 reviews)
"Nice affordable"

Reviewed on Jul 15, 2026

Wingate by Wyndham Louisville Fair and Expo
See all 1,679 properties in Simpsonville
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.
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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.
See properties

What to do in Simpsonville

Louisville: 3-Hour Food and History Tour of NuLu District

Louisville: 3-Hour Food and History Tour of NuLu District

CA $183
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

CA $28
per adult
92% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

CA $14
per adult
80% of travellers recommend
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour
See all activities in Simpsonville

Frequently asked questions

How much does a Simpsonville vacation package cost?
You can snap up a vacation package to this top destination from CA $1,086 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?

  1. 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.
  2. 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.
  3. 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.
  4. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, book the perfect Simpsonville vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.