Simpsonville Vacations from $791

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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.
Derby Hotel & Suites

Derby Hotel & Suites

2 out of 5
Save 100% on your flight
Price was $1,156, price is now $791 per person
$791
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
6.6/10 (88 reviews)
The bathroom was not clean at all. Tub was filthy. Stains all the sheets. Was supposed to be two queen bed suite and we got full size beds not nowhere near a suite! Most horrible experience! Will never be back

Reviewed on Jul 13, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Save 100% on your flight
Price was $3,840, price is now $2,264 per person
$2,264
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.6/10 Excellent! (1,006 reviews)
Laundry machines were not working, we were staying for a few days to do sports, it would have been nice to clean the uniforms. First night there, several cars were broken into. Right in front of the main door. I was getting ready and watching for the police to respond and it took almost 2 hours for them the show up. Several people were late to the game. Even refs.

Reviewed on Jul 12, 2026

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $1,704, price is now $1,126 per person
$1,126
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,002 reviews)
There wasn’t a hot tub. Room was big, bed comfortable.

Reviewed on Jul 13, 2026

The Duke Hotel

The Duke Hotel

2 out of 5
Downtown Louisville
Save 100% on your flight
Price was $1,584, price is now $1,097 per person
$1,097
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.6/10 Excellent! (19 reviews)
Found dead bugs; no other towels, bed sheets, or toiletries. No clean supplies available, and no one is coming to clean the place, especially since staying in the place for a long time.

Reviewed on Jun 16, 2026

Studio 6 Suites Louisville, KY – Airport/Expo Center

Studio 6 Suites Louisville, KY – Airport/Expo Center

2 out of 5
Highland Park
Save 100% on your flight
Price was $1,943, price is now $1,457 per person
$1,457
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
7.4/10 Good! (679 reviews)
When you arrive the facility is avg to below avg. it’s a motel set up. Doors to rooms are outside. Room was clean, AC blew cold, beds comfortable lots of hot water. Extra small bathroom. No hair dryer. Affordable place to stay close to fairgrounds

Reviewed on Jul 13, 2026

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Stay near popular Simpsonville attractions

The Outlet Shoppes of the Bluegrass

9.0/10 (69 reviews)
Kentucky's premier outlet shopping destination offers 80+ top brand stores in an elegant open-air setting. Browse Michael Kors and Coach while enjoying decorative fountains and covered walkways.
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What to do in Simpsonville

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

$25
per adult
92% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Louisville: 3-Hour Food and History Tour of NuLu District

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

$25
per adult
88% 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
$96 nightly
The price is $113 total per night from Jul 19 to Jul 20
$113 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (1,710 reviews)
"Nice sized rooms"

Reviewed on Jul 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
$119 nightly
The price is $140 total per night from Jul 22 to Jul 23
$140 total
Jul 22 - Jul 23
Total with taxes and fees
9.4/10 Exceptional! (2,358 reviews)
"Staff was pleasant and the hotel is impeccably maintained. My room was nicely furnished, large, and spotless. I’d definitely stay here again."

Reviewed on Jul 13, 2026

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
$65 nightly
The price is $76 total per night from Aug 13 to Aug 14
$76 total
Aug 13 - Aug 14
Total with taxes and fees
8.4/10 Very Good! (1,253 reviews)
"The room was small, but good for just a short stay. It was very clean and updated. The hallway smelled like an ashtray (old carpet?), but once in the room the smell was gone. Staff was very friendly."

Reviewed on Jul 13, 2026

Wingate by Wyndham Louisville Fair and Expo
See all 1,667 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 $791 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.