Hillsboro Vacations from $350

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The Latest Hillsboro vacation packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham St Louis Route 66

La Quinta Inn & Suites by Wyndham St Louis Route 66

3 out of 5
per person
Sep 18 - Sep 21
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to St. Louis (STL)
7.8/10 Good! (1,006 reviews)
Good for the price and clean

Reviewed on Jul 23, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
9/10 Wonderful! (1,549 reviews)
Did like the softness of the beds but thats just a personal preference. It wouldnt bother me but they felt just to soft. Like they just folded up.

Reviewed on Jul 28, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
8.2/10 Very Good! (756 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul 26, 2025

Comfort Inn Festus - St Louis South

Comfort Inn Festus - St Louis South

2.5 out of 5
per person
Oct 23 - Oct 27
found 1 hour ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
8/10 Very Good! (835 reviews)
Not a good place to stay for more than just a night. Place smells mushy and carpet is damp. The room was humid and the AC was just making it worse. Do not recommend this place at all.

Reviewed on Jul 19, 2025

Baymont by Wyndham Warrenton

Baymont by Wyndham Warrenton

2.5 out of 5
per person
Oct 23 - Oct 27
found 1 hour ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
7.4/10 Good! (971 reviews)
Great place to stay for softball in the summer!

Reviewed on Jul 28, 2025

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Hillsboro Hotel Deals

Historic Red Rooster Inn

Historic Red Rooster Inn

2 out of 5
123 E Seward St, Hillsboro, IL
$129 nightly
The price is $137 total per night from Jul 31 to Aug 1
$137 total
Jul 31 - Aug 1
Total includes taxes and fees
9.8/10 Exceptional! (17 reviews)
"This is such a unique place! It’s old, but has been completely remodeled and is so nice and clean. Will definitely stay here again when I’m in town!"

Reviewed on Jul 27, 2025

Historic Red Rooster Inn
Countryside Inn

Countryside Inn

2 out of 5
8105 IL-127, Hillsboro, IL
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $87 total per night from Jul 31 to Aug 1
$87 total
Jul 31 - Aug 1
Total includes taxes and fees
5.6/10 (35 reviews)
"Everything was clean and nice."

Reviewed on Jun 16, 2024

Countryside Inn
Charming Hillsboro Home < 1 Mi to Downtown!

Charming Hillsboro Home < 1 Mi to Downtown!

2 out of 5
Hillsboro
Get rates
Charming Hillsboro Home < 1 Mi to Downtown!
See all 46 properties in Hillsboro
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 Hillsboro Vacation Packages

Hillsboro Essential Information

Language
English
Currency
U.S dollars
Population
5,700
Top Sights
Litchfield Museum and Route 66 Welcome Center, Lake Lou Yeager and Raymond Shoal Creek Golf Course

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Frequently asked questions

How much does a Hillsboro vacation package cost?
You'll find cheap prices from $350 on Expedia for your Hillsboro escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Hillsboro costs.
What are the cheapest months to go to Hillsboro?
You can typically find lower rates and better availability in December, January and February. Take a look at our cheap Hillsboro vacation packages and you could score some excellent off-season deals.
How many days is enough for Hillsboro?
The ideal duration for your Hillsboro vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you time to hit all the top attractions and explore some hidden spots along the way.
How to find the best Hillsboro package deals?
Start your search for a Hillsboro package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Hillsboro package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hillsboro adventure underway.
Is it cheaper to book a Hillsboro vacation as a package?
You can enjoy significant savings on your Hillsboro retreat by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Hillsboro?
If you have your Hillsboro vacation dates finalized, book as early as you can to bag some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Hillsboro vacation packages?
If you're like us, you love traveling but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Hillsboro vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, 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.