Simpson Vacations from $229

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $267, price is now $229 per person
$229
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Paducah (PAH)
7.8/10 Good! (480 reviews)
Room was clean. Bed wasn't the most comfortable.

Reviewed on Dec 19, 2025

Holiday Inn Hotel & Suites Hopkinsville - Convention Ctr by IHG

Holiday Inn Hotel & Suites Hopkinsville - Convention Ctr by IHG

3 out of 5
Price was $567, price is now $485 per person
$485
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Paducah (PAH)
9.2/10 Wonderful! (169 reviews)
Everything was great, the room was very nice , the service was excellent and our requests were met in a timely manner. We visit Hopkinsville often, and would not consider staying with anyone else. Keep up the great work Andre & lillie

Reviewed on Dec 8, 2025

Holiday Inn Express Fort Campbell-Oak Grove by IHG

Holiday Inn Express Fort Campbell-Oak Grove by IHG

2.5 out of 5
Price was $498, price is now $429 per person
$429
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Paducah (PAH)
8.8/10 Excellent! (605 reviews)
Room was clean and staff was very nice. This was my second stay and I will come back again.

Reviewed on Dec 14, 2025

Sleep Inn & Suites Fort Campbell

Sleep Inn & Suites Fort Campbell

2.5 out of 5
Price was $428, price is now $369 per person
$369
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Paducah (PAH)
8.2/10 Very Good! (1,002 reviews)
Very clean and nice staff

Reviewed on Jan 5, 2026

Days Inn by Wyndham Oak Grove/Ft. Campbell

Days Inn by Wyndham Oak Grove/Ft. Campbell

2.5 out of 5
Price was $368, price is now $317 per person
$317
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Paducah (PAH)
7.2/10 Good! (232 reviews)
Room was clean and nice. Amenities were lacking. Bottles in shower were either stopped up or empty. They did have three tiny bottles on the sink but not enough for two persons. They did have baskets of shampoo & conditioner on the end of the counter in the offices but no one mentioned them and they had no body wash there. I didn’t notice them until later! Did not like kiosk check in and out. One other thing, if you have your iPhone near your door card, it erases your entry and you have to get someone to let you in.

Reviewed on Nov 28, 2025

Don't see what you're looking for?
See all available trips from Columbus to Simpson
View all trips

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 11 to Jan 12
$304 total
Jan 11 - Jan 12
Total with taxes and fees
10/10 Exceptional! (10 reviews)
Had great experience and host was very caring about everything being available and trying to make sure we had a wonderful stay

Reviewed on Dec 17, 2025

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Simpson vacation package cost?
You can pick up a vacation package to this popular destination from $229 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.