Simpson Vacations from $464

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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 $492, price is now $464 per person
$464
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Paducah (PAH)
7.8/10 Good! (480 reviews)
Room was clean. Bed wasn't the most comfortable.

Reviewed on Dec 19, 2025

Marcs Museum

Marcs Museum

3 out of 5
Price was $807, price is now $681 per person
$681
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Paducah (PAH)
No reviews
Residence Inn by Marriott Paducah

Residence Inn by Marriott Paducah

3 out of 5
Price was $553, price is now $517 per person
$517
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Paducah (PAH)
8.6/10 Excellent! (194 reviews)
Rooms were nice but we stopped after 13 hours of driving so our child could swim and the pools are closed for remodeling and that isn’t mentioned on the site.

Reviewed on Jan 3, 2026

The Respite Bed and Breakfast

The Respite Bed and Breakfast

4.5 out of 5
Price was $595, price is now $558 per person
$558
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Paducah (PAH)
9.8/10 Exceptional! (270 reviews)
Very clean room and staff was very courteous and hospitable. Enjoyed our stay very much.

Reviewed on Jan 5, 2026

Comfort Suites

Comfort Suites

2.5 out of 5
Price was $530, price is now $505 per person
$505
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Paducah (PAH)
8.6/10 Excellent! (900 reviews)
The desk staff were friendly and courteous. Quiet. They only clean after 3 nights. If you need something such as towels or amenities you have to request it.

Reviewed on Jan 7, 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
$180 nightly
The price is $191 total per night from Jan 11 to Jan 12
$191 total
Jan 11 - Jan 12
Total with taxes and fees
10/10 Exceptional! (14 reviews)
The cabin was spotless and had everything you could possibly need! The location is lovely and secluded but also close to area attractions!

Reviewed on Dec 1, 2025

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
$279 nightly
The price is $304 total per night from Jan 12 to Jan 13
$304 total
Jan 12 - Jan 13
Total with taxes and fees
10/10 Exceptional! (10 reviews)
The neat and clean bedding as well as all the available amenities at our reach. We mostly enjoyed how easy it was to find everything we needed.

Reviewed on Jan 5, 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
$65 nightly
The price is $78 total per night from Jan 22 to Jan 23
$78 total
Jan 22 - Jan 23
Total with taxes and fees
9.2/10 Wonderful! (1,017 reviews)
Everything was clean and smelled great. Staff were prompted and professional

Reviewed on Jan 5, 2026

Drury Inn & Suites Marion
See all 314 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 $464 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.