Simpson Vacations from $479

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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.

The Latest Simpson vacation packages

Price found within the past 48 hours. Click for updated prices.
Economy Inn & Suites

Economy Inn & Suites

2 out of 5
Price was $531, price is now $479 per person
$479
per person
Jun 12 - Jun 19
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Veterans Airport of Southern Illinois (MWA)
8.2/10 Very Good! (113 reviews)
The room was clean and the staff were very friendly.

Reviewed on Mar 11, 2026

DoubleTree by Hilton Mt. Vernon

DoubleTree by Hilton Mt. Vernon

4 out of 5
Price was $821, price is now $721 per person
$721
per person
Jun 12 - Jun 19
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Veterans Airport of Southern Illinois (MWA)
8.4/10 Very Good! (780 reviews)
I reserved a suite & got a standard room. I’m still being charged for a suite. I can’t get on contact with anyone.

Reviewed on Jan 23, 2026

Americas Best Value Inn West Frankfort

Americas Best Value Inn West Frankfort

2.5 out of 5
Price was $564, price is now $505 per person
$505
per person
Jun 12 - Jun 19
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Veterans Airport of Southern Illinois (MWA)
7.6/10 Good! (480 reviews)
The outside and lobby was clean. The young girl St the front desk was friendly and helpful. Th rooms were clean. The fridge was huge but looked a little rough on the outside but very clean on the inside. Beds weren’t too bad clean pillows soft. Bathroom has some tile broke sink was crewed to the wall. You can tell it wasn’t the original toilet that used to be in there didn’t match the spot on the floor and it moved when you sat firm on it. There was permanent stains on the tub But it was clean. Door was not put in tight padlock wouldn’t with but it had 2 other locks on it. Wasn’t that bad of a start but the room beside us they were arguing had a kids screaming and kept slamming their door really hard. Did it till about 11:30 at night. Kept waking us up throughout the night. Scared my daughter where she was afraid to go to sleep cause she thought someone was breaking in.

Reviewed on Feb 16, 2026

Fairgrounds Inn

Fairgrounds Inn

2 out of 5
Price was $663, price is now $594 per person
$594
per person
Jun 12 - Jun 19
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Veterans Airport of Southern Illinois (MWA)
7.6/10 Good! (398 reviews)
Everything was very nice

Reviewed on Mar 9, 2026

Holiday Inn Express Hotel & Suites Marion Northeast by IHG

Holiday Inn Express Hotel & Suites Marion Northeast by IHG

2.5 out of 5
Price was $1,010, price is now $920 per person
$920
per person
Jun 12 - Jun 19
found 1 hour ago
Roundtrip flight included
Chicago (CHI) to Veterans Airport of Southern Illinois (MWA)
9/10 Wonderful! (952 reviews)
Great plce! Friendly happy staff. Will definitely stay here again.

Reviewed on Mar 21, 2026

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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
$195 nightly
The price is $207 total per night from Mar 23 to Mar 24
$207 total
Mar 23 - Mar 24
Total with taxes and fees
10/10 Exceptional! (18 reviews)
Absolutely fantastic experience!

Reviewed on Mar 19, 2026

Cozy cabin, hot tub, high speed internet in the heart of the Shawnee
Luxury Glamping Dome w/ Hot Tub & Views

Luxury Glamping Dome w/ Hot Tub & Views

Simpson IL
$317 nightly
The price is $346 total per night from Mar 25 to Mar 26
$346 total
Mar 25 - Mar 26
Total with taxes and fees
10/10 Exceptional! (21 reviews)
Had everything we needed. Beautiful views

Reviewed on Mar 21, 2026

Luxury Glamping Dome w/ Hot Tub & 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
$95 nightly
The price is $114 total per night from Apr 20 to Apr 21
$114 total
Apr 20 - Apr 21
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
Friendly Staff, even with a late evening arrival. The room was clean and fresh and the linens smelled of fresh laundering. The breakfast was tasty. Perfect for our overnight stay!

Reviewed on Mar 20, 2026

Drury Inn & Suites Marion
See all 321 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 from $479 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.