Simpsonville Vacations from $435

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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.
Hilton Garden Inn Louisville/Northeast

Hilton Garden Inn Louisville/Northeast

3 out of 5
Save 100% on your flight
Price was $770, price is now $435 per person
$435
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9/10 Wonderful! (205 reviews)
Very clean. Good beds. Quiet. Supper available at the bar in the hotel.

Reviewed on Nov 17, 2025

Embassy Suites Louisville East

Embassy Suites Louisville East

3.5 out of 5
Save 100% on your flight
Price was $839, price is now $494 per person
$494
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Helpful staff, clean room and great amenities!

Reviewed on Nov 16, 2025

The Trail Hotel

The Trail Hotel

4 out of 5
Save 100% on your flight
Price was $717, price is now $468 per person
$468
per person
Feb 13 - Feb 16
found 12 hours ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
8.6/10 Excellent! (91 reviews)
Rooms were great and staff was wonderful.

Reviewed on Nov 22, 2025

Hancock House

Hancock House

3 out of 5
Downtown Louisville
Price was $707, price is now $483 per person
$483
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.2/10 Very Good! (245 reviews)
The apartment was so elegant with an antique vibe. It had high ceilings and lots of tall windows with drapes and blackout blinds. Modern stainless steel kitchen appliances. I really liked that it had an icemaker and lamps in every room. Besides the stairs you couldn’t hear the neighbors.The host made things even more convenient by providing late or early check in, late check out or the option to add an extra night right from the confirmation email of your booking. If you like wholesome comfort and simple amenities you would love this charming apartment stay.

Reviewed on Oct 31, 2025

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

3 out of 5
Price was $664, price is now $464 per person
$464
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (765 reviews)
Great customer service 👏

Reviewed on Nov 26, 2025

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Black Friday Sale

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Discover the most popular places to visit in Simpsonville

Ky Derby festival balloon glow.

Kentucky Exposition Center

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 showing horseriding and land animals as well as a small group of people

Churchill Downs

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

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

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
Derby City Ghosts: Louisville Hauntings Tour

Lace, Lunacy, and Loss: Louisville Ghost Tours

$32
per adult
Lace, Lunacy, and Loss: Louisville Ghost Tours
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
$72 nightly
The price is $85 total per night from Nov 30 to Dec 1
$85 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (979 reviews)
We stay here when we are attending events at the expo center and are always pleased!

Reviewed on Nov 21, 2025

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 Nov 30 to Dec 1
$140 total
Nov 30 - Dec 1
Total with taxes and fees
9.4/10 Exceptional! (1,631 reviews)
Clean room, lovely lobby and derby aesthetic was so nice! Fun to have the casino onsite and multiple bars and restaurants! Oliver’s was amazing! Will definitely be back!

Reviewed on Nov 25, 2025

Derby City Gaming & Hotel - A Churchill Downs Property
Courtyard by Marriott Louisville Airport

Courtyard by Marriott Louisville Airport

3 out of 5
819 Phillips Lane Louisville KY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $115 total per night from Nov 30 to Dec 1
$115 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (314 reviews)
Everything was so clean and staff was amazing

Reviewed on Nov 24, 2025

Courtyard by Marriott Louisville Airport
See all 1,668 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 $435 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.