Simpson Vacations from $528

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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.
Wingfield Inn

Wingfield Inn

2 out of 5
Price was $635, price is now $528 per person
$528
per person
Jan 12 - Jan 19
found 8 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Paducah (PAH)
7.8/10 Good! (622 reviews)

The Respite Bed and Breakfast

The Respite Bed and Breakfast

4.5 out of 5
Price was $1,042, price is now $828 per person
$828
per person
Jan 12 - Jan 19
found 8 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Paducah (PAH)
9.8/10 Exceptional! (370 reviews)
This was our second stay at the Respite and it was as good as the first. The rooms are beautiful and clean, the bed is comfortable and the breakfast is fabulous.

Reviewed on Nov 1, 2026

Quality Inn & Suites Metropolis I-24

Quality Inn & Suites Metropolis I-24

2.5 out of 5
Price was $664, price is now $541 per person
$541
per person
Jan 12 - Jan 19
found 8 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Paducah (PAH)
7.6/10 Good! (1,002 reviews)

Harrah's Metropolis Hotel & Casino - A Caesars Rewards Destination

Harrah's Metropolis Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $788, price is now $668 per person
$668
per person
Jan 12 - Jan 19
found 8 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Paducah (PAH)
8.4/10 Very Good! (1,005 reviews)
Hotel was very clean and well maintained

Reviewed on Nov 3, 2026

Holiday Inn Express Hotel & Suites Paducah West by IHG

Holiday Inn Express Hotel & Suites Paducah West by IHG

2.5 out of 5
Price was $851, price is now $731 per person
$731
per person
Jan 12 - Jan 19
found 8 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Paducah (PAH)
9.6/10 Exceptional! (1,000 reviews)

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Stay near popular Simpson attractions

Hogg Hollow Winery

9.4/10 (3 reviews)
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.
See properties

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
$231 nightly
The price is $231 total per night from Nov 30 to Dec 1
$231 total
Nov 30 - Dec 1
Total with taxes and fees
9.8/10 Exceptional! (42 reviews)
"Wonderful space. Everything you could need. Clean and bright!"

Reviewed on Oct 2, 2026

Cozy cabin, hot tub, high speed internet in the heart of the Shawnee
Quality Inn & Suites Metropolis I-24

Quality Inn & Suites Metropolis I-24

2.5 out of 5
2118 E 5th St Metropolis IL
Fully refundable
$56 nightly
The price is $62 total per night from Nov 29 to Nov 30
$62 total
Nov 29 - Nov 30
Total with taxes and fees
Quality Inn & Suites Metropolis I-24
Holiday Inn Express Metropolis by IHG

Holiday Inn Express Metropolis by IHG

2.5 out of 5
2179 East 5th Street Metropolis IL
Fully refundable
$83 nightly
The price is $92 total per night from Dec 2 to Dec 3
$92 total
Dec 2 - Dec 3
Total with taxes and fees
8.8/10 Excellent! (1,010 reviews)
"Breakfast was ok"

Reviewed on Nov 2, 2026

Holiday Inn Express Metropolis by IHG
See all 338 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 $528 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.