Simpsonville Vacations from $525
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Pillow and Paddock B&B
$608
per person
Nov 20 - Nov 22
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
10/10 Exceptional! (52 reviews)
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 2025
Don't see what you're looking for?
See all available trips from Columbus to Simpsonville
View all tripsStay 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.
Whitney M. Young, Jr. Birthplace
7.4/10 (11 reviews)
Tour the childhood home of civil rights leader Whitney M. Young Jr., preserved as an intimate museum. Explore personal artifacts and his replica NYC office by appointment for a meaningful glimpse into American history.
Shelby Trails Park
Roam through 460 acres of scenic trails at this equestrian haven, where woods and meadows beckon. Book a guided horseback ride or simply hike the 20 miles of diverse terrain, watching for wildlife along the way.
What to do in Simpsonville
Kentucky Derby Museum - General Admission and Guided Track Visit
$24
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
$129
per adult
94% of travellers recommend
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby
$29
per adult
92% of travellers recommend
Simpsonville Hotel Deals
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
$95 nightly
$112 total
Oct 28 - Oct 29
Total with taxes and fees
Crowne Plaza Louisville Airport Expo Ctr by IHG
830 Phillips Lane Louisville KY
Fully refundable
$101 nightly
$119 total
Oct 25 - Oct 26
Total with taxes and fees
8.8/10 Excellent! (1,889 reviews)
"Great hotel for the festival. Very clean and comfortable."
Reviewed on Oct 11, 2026
Wingate by Wyndham Louisville Fair and Expo
3200 Kemmons Drive Louisville KY
Fully refundableReserve now, pay when you stay
$70 nightly
$82 total
Nov 3 - Nov 4
Total with taxes and fees
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 |
More vacations you might like
Frequently asked questions
How much does a Simpsonville vacation package cost?
Offering excellent value package deals from $525 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?
- 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.
- 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.
- 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.
- 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.
- Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, lock in the ideal Simpsonville vacation package for you.
- 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.
Explore a world of travel with Expedia
- Frankfort Hotels
- Bardstown Hotels
- B&B in Simpsonville
- Red Roof Inn Hotels in Simpsonville
- Louisville Hotels
- Hotels near The Outlet Shoppes of the Bluegrass
- Lexington Hotels
- Hotels near Ark Encounter
- Marriott Hotels & Resorts in Simpsonville
- Hotels near Kentucky International Convention Center
- Shelbyville Hotels
- Cheap Hotels in Louisville
- Hotels near Kentucky Derby
- Downtown Louisville Hotels
- 5 Star Hotels in Simpsonville
- Pet-Friendly Hotels in Louisville
- Cabin Rentals in Simpsonville
- Simpsonville Hotels
- Hotels near Fourth Street Live!
- Hotels near Louisville Intl.
- Cabin Rentals in Louisville
- Motels in Simpsonville
- Hotels near Kentucky Exposition Center
- Cottages in Simpsonville
- Cabin Rentals in Kentucky
- Extended Stay Hotels in Louisville
- Hotels near KFC Yum Center
- Flights from Atlanta (ATL) to Louisville (SDF)
- Flights from Miami (MIA) to Louisville (SDF)
- Flights from Indianapolis (IND) to Louisville (SDF)
- Flights from Boston (BOS) to Louisville (SDF)
- Flights from New York (LGA) to Louisville (SDF)
- Flights to Kentucky
- Flights to Louisville
- Flights from Dallas (DFW) to Louisville (SDF)
- Flights to Simpsonville
- Flights from Las Vegas (LAS) to Louisville (SDF)
- Flights to Lexington
- Flights from Nashville (BNA) to Louisville (SDF)
- Flights from Simpsonville
- Flights from Orlando (MCO) to Louisville (SDF)
- Flights from Detroit (DTW) to Louisville (SDF)
- Flights from Seattle (SEA) to Louisville (SDF)
- Flights from Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
- Flights from Louisville Intl.
- Flights from Cincinnati (CVG) to Louisville (SDF)
- Flights from Los Angeles (LAX) to Louisville (SDF)
- Flights from Tampa (TPA) to Louisville (SDF)
- Flights from Charlotte (CLT) to Louisville (SDF)
- Flights from Philadelphia (PHL) to Louisville (SDF)
- Flights from Raleigh (RDU) to Louisville (SDF)
- Flights from New York (JFK) to Louisville (SDF)
- Flights from Houston (HOU) to Louisville (SDF)
- Flights from Denver (DEN) to Louisville (SDF)
- Flights from Portland (PDX) to Louisville (SDF)
- Flights from Chicago (ORD) to Louisville (SDF)
- Flights from Blue Grass
- Flights from Phoenix (PHX) to Louisville (SDF)
- Flights from Washington (DCA) to Louisville (SDF)
- Flights from Minneapolis (MSP) to Louisville (SDF)
- Flights from Fort Lauderdale (FLL) to Louisville (SDF)
- The Outlet Shoppes of the Bluegrass
- Shelbyville Vacations
- Louisville Mega Cavern
- Danger Run
- Village Square Shopping Center
- Kentucky State Capitol
- Iceland Sports Complex
- Louisville Zoo
- Yew Dell Botanical Gardens
- Pewee Valley Vacations
- Beckley Creek Park
- The Red Scooter
- Louisville Slugger Museum
- Springhurst Towne Center Shopping Center
- Where to stay in Louisville
- Eastgate Shopping Center
- E.p. Tom Sawyer State Park
- Jeffersontown Commons Shopping Center
- Eagle Creek Golf Course
- Chenoweth Park
- The Kentucky Castle
- Gallrein Farms
- Middletown Station Shopping Center
- Southeast Christian Church
- Weissinger Hills Golf Course
- Ark Encounter
- Bluegrass Indoor Karting
- Hurstbourne Corners Shopping Center
- Kentucky Vacations
- Stonefield Square Shopping Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
