Simpson Vacations from $425

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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.
Red Roof Inn Murray

Red Roof Inn Murray

3 out of 5
Price was $438, price is now $425 per person
$425
per person
Jun 26 - Jun 29
found 15 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Paducah (PAH)
6.4/10 (613 reviews)
Very clean, quiet, nice staff 👌

Reviewed on Apr 10, 2026

The Lakehouse Inn at Sledd Creek

The Lakehouse Inn at Sledd Creek

2 out of 5
Price was $1,334, price is now $1,220 per person
$1,220
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Sacramento (SMF) to Paducah (PAH)
10/10 Exceptional! (153 reviews)
It was very clean. The decor was amazing. The staff was so kind. This is definitely a place we will be returning to.

Reviewed on May 1, 2026

Holiday Inn Express Metropolis by IHG

Holiday Inn Express Metropolis by IHG

2.5 out of 5
Price was $631, price is now $581 per person
$581
per person
Jun 26 - Jun 29
found 15 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Paducah (PAH)
8.6/10 Excellent! (1,004 reviews)
Pet friendly. Pleasant staff. Room was close to Lobby and breakfast area and was a little loud during set up.

Reviewed on May 5, 2026

The Meadows Hotel

The Meadows Hotel

3.5 out of 5
Price was $708, price is now $675 per person
$675
per person
Jul 12 - Jul 17
found 2 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to Paducah (PAH)
9.2/10 Wonderful! (260 reviews)
Very unique property. Pretty. Old but refurbished beautifully. Music from dining room was bothersome & kept us from getting to sleep. We were put in a handicapped room( not needed but was only room available) that was beautiful but every time we used bathroom at night, the light automatically came on. Also the light above the door flashed off & on. We were able to turn it off. One of the bedside lamps didn’t work. Burned out bulb I suppose. We were given a $5 voucher each for breakfast at a nearby diner that was delightful.

Reviewed on May 4, 2026

Garner Hotel Paducah West by IHG

Garner Hotel Paducah West by IHG

2.5 out of 5
Price was $583, price is now $562 per person
$562
per person
Jun 26 - Jun 29
found 15 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Paducah (PAH)
8.6/10 Excellent! (120 reviews)
Our room was super clean and up to date! The front desk staff were super polite and efficient! They were able to quickly solve our problems with accessing the internet! The breakfast was just what we expected - and the staff in the breakfast area were super friendly!!! The parking was plentiful and safe! We were very pleased with our two night stay!!!

Reviewed on Apr 28, 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
$176 nightly
The price is $187 total per night from May 20 to May 21
$187 total
May 20 - May 21
Total with taxes and fees
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
$298 nightly
The price is $325 total per night from May 12 to May 13
$325 total
May 12 - May 13
Total with taxes and fees
10/10 Exceptional! (22 reviews)
Absolute must stay! Incredible experience celebrating with my wife for our anniversary!

Reviewed on Apr 27, 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
$93 nightly
The price is $112 total per night from Jun 7 to Jun 8
$112 total
Jun 7 - Jun 8
Total with taxes and fees
9.4/10 Exceptional! (1,009 reviews)
I’ve stayed here before. They always meet expectations. Clean facilities (inside & out). Staff is available and helpful. The evening cocktail (on the house) is nice after a long drive if you have a chance to relax a partake.

Reviewed on May 5, 2026

Drury Inn & Suites Marion
See all 317 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 $425 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.