A brick clock tower with two clocks, surrounded by dense foliage.

Simpsonville Vacations from $564

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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.
  • Jan 14 - Jan 17

    The Grady + Flight

    Downtown Louisville
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,006 reviews)
    "Property and location are outstanding. The wild swan restaurant is amazing and if you have the chance to meet Mark, you get the history of the hotel and get to have the service you would want. Mark was fantastic and was the highlight of the hotel for us. Everything is spotless and clean. Great service and great food!"
    Reviewed November 4, 2026
    Roundtrip • San Diego (SAN) - Louisville (SDF)
    SAN - SDF • 1 stop SDF - SAN • 1 stop
    $690
    $564
    per traveler
    found 12 hours ago
    The Grady
  • Dec 8 - Dec 13

    Pillow and Paddock B&B + Flight

    La Grange
    5 nights
    3.5 star property
    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 December 22, 2025
    Roundtrip • San Diego (SAN) - Louisville (SDF)
    SAN - SDF • 1 stop SDF - SAN • 1 stop
    $2,477
    $1,955
    per traveler
    found 9 hours ago
    Pillow and Paddock B&B
  • Dec 30 - Jan 5

    Cottonwood Airport & Expo Hotel Louisville + Flight

    Shively
    6 nights
    3.5 star property
    8.8/10 - Excellent (1,002 reviews)
    Roundtrip • Dallas (DFW) - Louisville (SDF)
    DFW - SDF • Nonstop SDF - DFW • Nonstop
    $773
    $626
    per traveler
    found 1 day ago
    Cottonwood Airport & Expo Hotel Louisville
  • Dec 30 - Jan 5

    Hotel Distil, Autograph Collection + Flight

    Downtown Louisville
    6 nights
    4.0 star property
    9.6/10 - Exceptional (517 reviews)
    Roundtrip • Dallas (DFW) - Louisville (SDF)
    DFW - SDF • Nonstop SDF - DFW • Nonstop
    $1,229
    $1,003
    per traveler
    found 1 day ago
    Hotel Distil, Autograph Collection
  • Dec 8 - Dec 13

    The Purple Martin + Flight

    Prospect
    5 nights
    2.0 star property
    10/10 - Exceptional (2 reviews)
    "Amazing property… I would come back in a heartbeat! "
    Reviewed June 19, 2025
    Roundtrip • San Diego (SAN) - Louisville (SDF)
    SAN - SDF • 1 stop SDF - SAN • 1 stop
    $1,995
    $1,655
    per traveler
    found 9 hours ago
    The Purple Martin

Where to stay in Simpsonville

Discover the charm of the Simpsonville, Kentucky area, where family-friendly districts and inviting atmospheres await. Venture to nearby downtown Louisville for vibrant art and sports experiences. The best time to explore is when the community comes alive, making your visit truly memorable.

Louisville

Discover Louisville, a vibrant city that caters to family travelers seeking a mix of culture and outdoor fun. With attractions like the Kentucky Exposition Center and the Louisville Slugger Museum, there's plenty to explore. Situated within Louisville, Simpsonville offers easy access to shopping centers and recreational areas, making it an ideal base for your adventures. Choose Louisville for your stay, where the diverse experiences will make your trip memorable.

Finchville

Experience the charm of Finchville, an excellent hub for families and outdoor enthusiasts looking for a blend of recreation and relaxation. Just a short drive from Simpsonville, Finchville offers access to the scenic Taylorsville Lake and the inviting Taylorsville Lake State Park, perfect for a day of hiking or picnicking. Visitors can also explore local attractions like the Whitney M. Young, Jr. Birthplace. With its convenient location and diverse activities, Finchville is a smart choice for your next getaway.

Shelbyville

Make your vacation planning effortless by staying in Shelbyville, a haven for family travelers seeking outdoor adventures and romantic getaways. With attractions like Guist Creek Lake State Park for nature lovers, Gallrein Farms for a taste of local charm, and the historic Whitney M. Young, Jr. Birthplace, there’s something for everyone to enjoy. Located about 7 miles by car from Simpsonville, Shelbyville offers easy access and a welcoming atmosphere, making it a smart choice for your stay.

Eastwood

Eastwood stands out as a prime spot for travelers seeking a blend of outdoor adventure and urban experiences. Here, visitors can explore the serene E.P. Tom Sawyer State Park, enjoy shopping at nearby centers, and unwind at the picturesque lake. Located about 7 miles by car from Simpsonville, Eastwood offers easy access to its attractions, making it an ideal choice for families and weekend getaways. With its welcoming environment, Eastwood is a smart hotel booking choice for your Kentucky vacation.

Fisherville

Looking for the perfect spot? Fisherville is ideal for travelers seeking a blend of nature and family-friendly activities with its beautiful Beckley Creek Park and engaging local theater scene. Visitors can enjoy outdoor adventures or relax at the nearby lake, making it a delightful retreat year-round. Located about 6 miles by car from Simpsonville, Fisherville offers easy access to various attractions while providing a charming atmosphere perfect for a memorable stay.

Discover the most popular places to visit in Simpsonville

What to do in Simpsonville

Simpsonville Hotel Deals

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.

Frequently Asked Questions

How much does a Simpsonville vacation package cost?

Offering excellent value package deals from $564 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.