Simpson Vacations

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Your Simpson Vacation

When you choose a Simpson vacation package, you can relax and enjoy your adventure to the fullest. Discover the highlights of this unique city knowing that all your travel needs have been organized in advance. Eager to tour the sights but don't know where to start? Any trip to Simpson should include Hogg Hollow Winery. Check out Expedia's wide range of travel options and begin planning your ultimate vacation to Simpson today.

Discover the most popular places to visit in Simpson

Hogg Hollow Winery

You can enjoy a tasting or tour at Hogg Hollow Winery during your travels to Simpson. Wander the gardens and parks while you're in the area.

Hogg Hollow Winery

Simpson Hotel Deals

Cozy cabin, hot tub, high speed internet in the heart of the Shawnee

Cozy cabin, hot tub, high speed internet in the heart of the Shawnee

Simpson IL
$211 nightly
The price is $224 total per night from Jun 24 to Jun 25
$224 total
Jun 24 - Jun 25
Total with taxes and fees
10/10 Exceptional! (27 reviews)
"Was very pleased with the property! Would like to come back in the future!!"

Reviewed on Jun 8, 2026

Cozy cabin, hot tub, high speed internet in the heart of the Shawnee
Glamping Dome · Hot Tub, Fire Pit & Forest Views

Glamping Dome · Hot Tub, Fire Pit & Forest Views

Simpson IL
$333 nightly
The price is $364 total per night from Jul 12 to Jul 13
$364 total
Jul 12 - Jul 13
Total with taxes and fees
10/10 Exceptional! (24 reviews)
"We had a wonderful weekend and the Glamping Globe was such a unique experience. Highly recommend!"

Reviewed on Jun 10, 2026

Glamping Dome · Hot Tub, Fire Pit & Forest Views
Drury Inn & Suites Marion

Drury Inn & Suites Marion

3 out of 5
2706 W DeYoung St Marion IL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $113 total per night from Jun 29 to Jun 30
$113 total
Jun 29 - Jun 30
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
"The property was very clean, breakfast had good variety, and staff were friendly and helpful."

Reviewed on Jun 18, 2026

Drury Inn & Suites Marion
See all 325 properties in Simpson
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 Simpson Vacation Packages

Simpson Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Williamson County Regional Airport (MWA)
Top Sights
Dixon Springs State Park, Hogg Hollow Winery and The Chocolate Factory

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Frequently asked questions

How much does a Simpson vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But how much your vacation to Simpson costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Simpson?
You can typically find lower rates and greater availability in December, January and February. Take a look at our cheap Simpson vacation packages and you could land some great off-season deals.
How many days is enough for Simpson?
Usually, a handful of days is enough to see the top sights during your Simpson vacation. But if you want to have more time to relax or take day tours, think about extending your itinerary.
How to find the best Simpson package deals?
Use Expedia's filter tool to help you find some fabulous Simpson package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Simpson package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Simpson vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Simpson vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Simpson?
If you're considering a spontaneous Simpson trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Simpson vacation packages?
If you're like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Simpson break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.