Simpsonville Vacations from $563

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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.
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was $756, price is now $563 per person
$563
per person
Jun 28 - Jul 4
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,266 reviews)
We had a great stay. No free breakfast, but restaurant on site to order. Walkable to the expo center.

Reviewed on Apr 12, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $1,207, price is now $873 per person
$873
per person
Jun 28 - Jul 4
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Nice, clean and convenient

Reviewed on Mar 29, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was $828, price is now $611 per person
$611
per person
Jun 28 - Jul 4
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.6/10 Excellent! (1,009 reviews)
I had a wonderful stay at the Cottonwood Airport & Expo Hotel Louisville. The staff were incredibly kind, friendly, professional, and knowledgeable. Truly exceptional service from start to finish. The hotel and rooms were clean, comfortable, and well-maintained, I enjoyed my stay and would return. I recommend it to others!

Reviewed on Apr 10, 2026

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
Downtown Louisville
Price was $879, price is now $678 per person
$678
per person
Jun 28 - Jul 4
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (4,130 reviews)
It's my fault for not realizing the balconies facing the river are also located above the highway. I was not able to sit outside in the night or morning due to the insane traffic noise. Again, my fault for not researching more. Paid a premium rate for the room and couldn't even use it.

Reviewed on Apr 13, 2026

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

3 out of 5
Price was $868, price is now $688 per person
$688
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Louisville (SDF)
No reviews
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Discover the most popular places to visit in Simpsonville

Kentucky Exposition Center

Kentucky Exposition Center

4.5/5(636 reviews)

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

Kentucky Exposition Center
Churchill Downs

Churchill Downs

4.5/5(555 reviews)

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

Churchill Downs
Panorama Ohio River waterway riverboats and bridges leading to heart of downtown Louisville KY

KFC Yum Center

4.5/5(426 reviews)

Catch an event at KFC Yum Center during your trip to Louisville. Stroll along the riverfront or attend a sporting event in the area.

KFC Yum Center

What to do in Simpsonville

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

$22
per adult
90% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Louisville: NuLu District Food and History Tour

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

$129
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Kentucky Derby Museum - Admission with Guided Track Visit

Kentucky Derby Museum - Admission with Guided Track Visit

$22
per adult
100% of travellers recommend
Kentucky Derby Museum - Admission with Guided Track Visit
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 $110 total per night from Apr 19 to Apr 20
$110 total
Apr 19 - Apr 20
Total with taxes and fees
8.8/10 Excellent! (1,294 reviews)
Far too expensive for what they deliver. We had to call 4 times to get someone up to free up the corridor from loud party guys at 1 am, they even nocked on bedroom doors. The breakfast was dry/over cooked. Not to repeat

Reviewed on Apr 13, 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
$113 nightly
The price is $133 total per night from Apr 19 to Apr 20
$133 total
Apr 19 - Apr 20
Total with taxes and fees
9.4/10 Exceptional! (1,960 reviews)
Beautiful rooms, friendly staff, very clean and classy

Reviewed on Apr 12, 2026

Derby City Gaming & Hotel - A Churchill Downs Property
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
$122 nightly
The price is $144 total per night from May 10 to May 11
$144 total
May 10 - May 11
Total with taxes and fees
9.4/10 Exceptional! (985 reviews)
Nice hotel.

Reviewed on Apr 12, 2026

Tempo By Hilton Louisville Downtown Nulu
See all 1,742 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 $563 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.

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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.