Simpsonville Vacations from $500

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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.
La Quinta Inn & Suites by Wyndham Bardstown

La Quinta Inn & Suites by Wyndham Bardstown

3 out of 5
Price was $570, price is now $500 per person
$500
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
9.2/10 Wonderful! (1,103 reviews)
Looks new, Been there 5 years. Well taken care of property. You can hear people above you walking so building isn't built with buffering that in mind

Reviewed on May 27, 2026

Hampton Inn Louisville-Airport

Hampton Inn Louisville-Airport

2.5 out of 5
Fairgrounds
Price was $926, price is now $752 per person
$752
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.6/10 Excellent! (1,003 reviews)
The rooms were very clean and the staff was very friendly

Reviewed on May 28, 2026

Staybridge Suites - Louisville - East by IHG

Staybridge Suites - Louisville - East by IHG

3 out of 5
Middletown
Price was $730, price is now $594 per person
$594
per person
Aug 1 - Aug 8
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.2/10 Very Good! (712 reviews)
The staff was friendly and helpful, the room was clean and breakfast was very good. We had a great stay.

Reviewed on May 10, 2026

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94

2 out of 5
Price was $654, price is now $548 per person
$548
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
8.8/10 Excellent! (1,579 reviews)
Large room, jetted tub, excellentvarea

Reviewed on May 29, 2026

Central Park Bed & Breakfast

Central Park Bed & Breakfast

3.5 out of 5
Old Louisville
Price was $828, price is now $723 per person
$723
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.2/10 Wonderful! (79 reviews)
Such a lovely building, clearly loved by all who work there. Information about the property, check-in procedure, etc. was communicated very clearly before my arrival. Fresh lemon blueberry scones were there for a snack when I arrived near midnight. Wow. When booking, I didn’t think about the lack of elevator at this property. My 68 year old knees did complain a little when climbing the external & interior stairs with my luggage.

Reviewed on May 22, 2026

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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 acclaimed theater scene and great live music.

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
Louisville Slugger Museum

Louisville Slugger Museum

4.5/5(613 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

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
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
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
See all activities in Simpsonville

Simpsonville Hotel Deals

Hampton Inn Simpsonville

Hampton Inn Simpsonville

2.5 out of 5
814 Aristocrat Ct Simpsonville KY
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $102 total per night from Jun 7 to Jun 8
$102 total
Jun 7 - Jun 8
Total with taxes and fees
9.4/10 Exceptional! (960 reviews)
"Friendly staff; rooms and bathrooms were clean"

Reviewed on May 25, 2026

Hampton Inn Simpsonville
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
$82 nightly
The price is $97 total per night from Jun 28 to Jun 29
$97 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (1,478 reviews)
"Great hotel. Would definitely stay here again."

Reviewed on May 29, 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 May 31 to Jun 1
$133 total
May 31 - Jun 1
Total with taxes and fees
9.4/10 Exceptional! (2,146 reviews)
"Very comfortable and clean room. Perfect start to our vacation"

Reviewed on May 29, 2026

Derby City Gaming & Hotel - A Churchill Downs Property
See all 1,749 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 $500 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.