Simpson Vacations from $368

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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.
Unity Lodge

Unity Lodge

2 out of 5
Price was $417, price is now $368 per person
$368
per person
Aug 14 - Aug 16
found 21 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Paducah (PAH)
7.4/10 Good! (49 reviews)
Was difficult to find they need to put up a eligible sign and fix the road going into parking lot

Reviewed on Oct 25, 2024

Best Western Hopkinsville KY - Brand New Rooms

Best Western Hopkinsville KY - Brand New Rooms

2.5 out of 5
Price was $594, price is now $493 per person
$493
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Paducah (PAH)
8.4/10 Very Good! (235 reviews)
I have stayed at Best Western several times the staff member are very helpful kind and friendly also the host HeMal is always a pleasure to see thank you for maintaining your property and the breakfast is always good and delicious. Thank you Paulette Desmore

Reviewed on May 26, 2026

The Respite Bed and Breakfast

The Respite Bed and Breakfast

4.5 out of 5
Price was $501, price is now $434 per person
$434
per person
Aug 14 - Aug 16
found 21 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Paducah (PAH)
9.8/10 Exceptional! (327 reviews)
Great location. Nice accommodation.

Reviewed on Jun 4, 2026

La Quinta Inn & Suites by Wyndham Hopkinsville

La Quinta Inn & Suites by Wyndham Hopkinsville

3 out of 5
Price was $505, price is now $439 per person
$439
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Paducah (PAH)
7.8/10 Good! (1,003 reviews)
Lady at the desk was extremely helpful and gracious! Breakfast is always a treat during my stays!😋 Hotel was in the midst of renovations and pool was closed but I still had a wonderful stay! Look forward to my next stay!

Reviewed on Jun 2, 2026

Belle Louise Historic Guest House

Belle Louise Historic Guest House

3.5 out of 5
Price was $704, price is now $611 per person
$611
per person
Aug 14 - Aug 16
found 21 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Paducah (PAH)
10/10 Exceptional! (13 reviews)
Good location and great owners

Reviewed on Apr 22, 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
$229 nightly
The price is $243 total per night from Jun 22 to Jun 23
$243 total
Jun 22 - Jun 23
Total with taxes and fees
10/10 Exceptional! (25 reviews)
"We had a wonderful mini-vacation here! The property was incredibly clean, peaceful, and well-maintained. The hot tub was a massive highlight and the perfect way to unwind in the evenings. Highly recommend this spot for a relaxing getaway!"

Reviewed on May 20, 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
$354 nightly
The price is $386 total per night from Jun 16 to Jun 17
$386 total
Jun 16 - Jun 17
Total with taxes and fees
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 $111 total per night from Jun 28 to Jun 29
$111 total
Jun 28 - Jun 29
Total with taxes and fees
Drury Inn & Suites Marion
See all 323 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 $368 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.