Simpson Vacations

Book a Hotel + Flight or Car together to unlock savings

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

Hot tub. hiking, biking, fishing, swimming, rock climbing or just sight seeing.

Hot tub. hiking, biking, fishing, swimming, rock climbing or just sight seeing.

Golconda
$149 nightly
The price is $158 total per night from Nov 14 to Nov 15
$158 total
Nov 14 - Nov 15
Total with taxes and fees
10/10 Exceptional! (20 reviews)
It was the perfect getaway to relax and beautiful area. The owners are very welcoming and nice .. My husband and I usually never go back to the same place twice. We will be back we both really enjoyed our time there. Thank you ..

Reviewed on Nov 3, 2025

Hot tub. hiking, biking, fishing, swimming, rock climbing or just sight seeing.
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
$215 nightly
The price is $228 total per night from Nov 13 to Nov 14
$228 total
Nov 13 - Nov 14
Total with taxes and fees
10/10 Exceptional! (9 reviews)
Very clean, loved the hot tub. Good location

Reviewed on Oct 26, 2025

Cozy cabin, hot tub, high speed internet in the heart of the Shawnee
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
$65 nightly
The price is $78 total per night from Nov 24 to Nov 25
$78 total
Nov 24 - Nov 25
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Clean

Reviewed on Nov 3, 2025

Drury Inn & Suites Marion
See all 308 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.