Simpsonville Vacations from $527

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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.

The Latest Simpsonville vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Louisville Airport - Fair/Expo by IHG

Holiday Inn Louisville Airport - Fair/Expo by IHG

3 out of 5
Fairgrounds
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
8.2/10 Very Good! (839 reviews)
A large room very clean.

Reviewed on Jun 29, 2025

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
Save 100% on your flight
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9.4/10 Exceptional! (1,265 reviews)
Extremely clean, beautifully decorated and very fun atmosphere. Very nice staff as well.

Reviewed on Jul 12, 2025

Tempo By Hilton Louisville Downtown Nulu

Tempo By Hilton Louisville Downtown Nulu

3.5 out of 5
Downtown Louisville
per person
Sep 17 - Sep 22
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9.4/10 Exceptional! (635 reviews)
Great place Would have got 5 stars BUT !!!!! WORST BED EVER GRAND CANYON WHERE OTHER PEOPLE SLEPT!!!! Otherwise we loved it

Reviewed on Jul 10, 2025

Homewood Suites by Hilton Louisville-East

Homewood Suites by Hilton Louisville-East

3 out of 5
per person
Sep 17 - Sep 22
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9.6/10 Exceptional! (618 reviews)
The property itself was great. Very clean, very quiet, rooms were excellent. However we experienced something terrible with an employee of the hotel. We had been swimming and the maintenance/pool man had come out to test the pool water. My 2 grandsons were swimming at the other end. He walked over to our chairs where we had Been sitting by the pool and said, I have to throw 2 cups of baking soda into the water because the PH level is a little low but it won’t hurt anyone…. (Here it comes) he continues to say “if anything it will turn those kids white”. Those kids happened to be MY GRANDSONS! , who are black! (Keep in mind, I am white). I don’t think he knew those kids were with us…. What a horrible racist remark. I did tell the front desk at checkout. I really hope they speak to this employee.

Reviewed on Jun 29, 2025

Towneplace Suites By Marriott Louisville Downtown

Towneplace Suites By Marriott Louisville Downtown

3 out of 5
Downtown Louisville
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9/10 Wonderful! (409 reviews)
Bill at the Front desk was awesome. Pool was a little smallish and cold. Breakfast was excellent.

Reviewed on Jul 12, 2025

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Discover the most popular places to visit in Simpsonville

Ky Derby festival balloon glow.

Kentucky Exposition Center

4.5/5(628 reviews)

Learn about the events happening at Kentucky Exposition Center during your trip to Louisville. Experience the area's lively festivals and great live music.

Kentucky Exposition Center
Churchill Downs showing horseriding and land animals as well as a small group of people

Churchill Downs

4.5/5(551 reviews)

Find more than mint juleps to enjoy at this iconic racetrack, best known as the annual host of the Kentucky Derby.

Churchill Downs
Louisville Slugger Museum showing interior views

Louisville Slugger Museum

4.5/5(606 reviews)

Baseball is part of the American fabric. See where one important tool for this sport is produced in the factory that makes ball games possible.

Louisville Slugger Museum

What to do in Simpsonville

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

$30
per traveler
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
Historic Old Louisville Walking Tour

Historic Old Louisville Walking Tour

$15
per adult
100% of travellers recommend
Historic Old Louisville Walking Tour
Louisville: Photoshoot Walking Tour with Pictures

Louisville: Photoshoot Walking Tour with Pictures

$55
per adult
Louisville: Photoshoot Walking Tour with Pictures
See all activities in Simpsonville

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 refundableReserve now, pay when you stay
$94 nightly
The price is $111 total per night from Jul 21 to Jul 22
$111 total
Jul 21 - Jul 22
Total includes taxes and fees
8.6/10 Excellent! (644 reviews)
"Comfortable"

Reviewed on Jul 11, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Wingate by Wyndham Louisville Fair and Expo
Wingate by Wyndham Louisville Fair and Expo
2.5 out of 5
3200 Kemmons Drive, Louisville, KY
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $76 total per night from Aug 4 to Aug 5
$76 total
Aug 4 - Aug 5
Total includes taxes and fees
8.4/10 Very Good! (1,097 reviews)
"Really friendly staff and the front desk! And the building smelled good when we walked in."

Reviewed on Jul 13, 2025

Wingate by Wyndham Louisville Fair and Expo
Tempo By Hilton Louisville Downtown Nulu
Tempo By Hilton Louisville Downtown Nulu
3.5 out of 5
710 E Jefferson Street, Louisville, KY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jul 17 to Jul 18
$149 total
Jul 17 - Jul 18
Total includes taxes and fees
9.4/10 Exceptional! (643 reviews)
"Great place Would have got 5 stars BUT !!!!! WORST BED EVER GRAND CANYON WHERE OTHER PEOPLE SLEPT!!!! Otherwise we loved it"

Reviewed on Jul 10, 2025

Tempo By Hilton Louisville Downtown Nulu
See all 1,621 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.

Find the Best Simpsonville Vacation Packages

Simpsonville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Louisville Intl. Airport (SDF)
Population
2,700
Top Sights
Kentucky Artisan Distillery, Talon Winery and Shelby County Community Theatre

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Frequently asked questions

How much does a Simpsonville vacation package cost?
Offering excellent value package deals from $527 on Expedia, you'll be thrilled with how little a vacation to Simpsonville costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Simpsonville?
May, August and December are the best times to look for cheap Simpsonville vacation packages. Traveling in quieter months means you can typically find lower prices on hotels and flights.
How many days is enough for Simpsonville?
Usually, a handful of days is enough to see the top sights during your Simpsonville vacation. However, if you prefer to have time to kick back or go on day trips, consider extending your itinerary.
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 busy. Whether you're traveling with the family or getting away with friends, a Simpsonville vacation promises fun for everyone.
How to find the best Simpsonville package deals?
Landing a cheap Simpsonville package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Simpsonville package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Simpsonville vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can personalize your Simpsonville escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Simpsonville?
If you have your Simpsonville travel dates confirmed, book as early as you can to snap up some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for traveling on a whim.
How to plan a trip to Simpsonville?

  1. Choose when to travel: Check your diary and get packing. Your favorite season and the activities available will also help you decide when to escape to Simpsonville.
  2. Plan your budget wisely: Besides the cost of your accommodations, you'll need to factor in other expenses too. These include flights, food and transportation. Also, put aside a little extra for unexpected costs that could crop up during your trip to Simpsonville.
  3. Discover Simpsonville using Expedia's trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Simpsonville. You can also save your favorite places, collaborate with family and friends and organize your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Simpsonville, you can figure out the right length of your break. Create a draft plan and allocate enough time for all the things you want to do.
  5. Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, lock in the ideal Simpsonville vacation package for you.
  6. Add on excursions and experiences: Take a look at our travel guide to find some exciting things to do in Simpsonville. Book tickets or make reservations before you go to save time and avoid the stress of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Simpsonville vacation packages?
Your Simpsonville getaway is meant to be an escape from your daily routine, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.