Hillsboro Vacations from $271

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Your Hillsboro Vacation

Our Hillsboro vacation packages let you customize your own adventure. Tailor your getaway to your interests and needs and make every moment count in this fabulous city. Villa Antonio Winery, Sandy Creek Covered Bridge State Historic Site and Victoria Glaces Conservation Area Trailhead are just some of the sights you'll want to check out during your trip to Hillsboro. A few clicks is all it takes to build a tailored Hillsboro vacation on Expedia.

The Latest Hillsboro vacation packages

Price found within the past 48 hours. Click for updated prices.
The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $345, price is now $271 per person
$271
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
9.4/10 Exceptional! (425 reviews)
Very friendly and helpful front desk staff and restaurant staff. Lovely experience!

Reviewed on Feb 4, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $669, price is now $501 per person
$501
per person
Apr 16 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Great room and friendly staff in a nice area. Will come again.

Reviewed on Feb 11, 2026

Landing Apartments - Eureka

Landing Apartments - Eureka

4 out of 5
Price was $1,223, price is now $936 per person
$936
per person
Mar 25 - Mar 29
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to St. Louis (STL)
No reviews
Spacious 3-Bedroom with King Bed

Spacious 3-Bedroom with King Bed

4 out of 5
Central West End
Save 100% on your flight
Price was $679, price is now $542 per person
$542
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.6/10 Excellent! (10 reviews)
Clean room nice area

Reviewed on Feb 1, 2026

Holiday Inn Express Troy by IHG

Holiday Inn Express Troy by IHG

2.5 out of 5
Price was $447, price is now $362 per person
$362
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to St. Louis (STL)
9.4/10 Exceptional! (688 reviews)
Clean room. Helpful staff.

Reviewed on Feb 11, 2026

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Discover the most popular places to visit in Hillsboro

Villa Antonio Winery

You can enjoy a tasting or tour at Villa Antonio Winery during your travels to Hillsboro. Discover the area's countryside and churches.

Villa Antonio Winery

Sandy Creek Covered Bridge State Historic Site

You can find out about the history of Hillsboro with a stop at Sandy Creek Covered Bridge State Historic Site. Discover the area's sunrises and churches.

Sandy Creek Covered Bridge State Historic Site

Sunridge Park

Explore the great outdoors at Sunridge Park, a lovely green space in Hillsboro. Amble within the natural setting or visit the churches in this family-friendly area.

Sunridge Park

Hillsboro Hotel Deals

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

3 out of 5
1088 South Highway Drive Fenton MO
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from Feb 15 to Feb 16
$103 total
Feb 15 - Feb 16
Total with taxes and fees
7.8/10 Good! (1,097 reviews)
Coffee!! And the breakfast. Both were fantastic! Room was clean and nice except for the heating. Didn’t get much sleep due to a very noisy heating unit. Friendly people at check in and out.

Reviewed on Feb 8, 2026

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham
River City Casino & Hotel

River City Casino & Hotel

4 out of 5
777 River City Casino Blvd St. Louis MO
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $121 total per night from Feb 18 to Feb 19
$121 total
Feb 18 - Feb 19
Total with taxes and fees
9/10 Wonderful! (1,482 reviews)
Clean, quiet, comfortable; friendly staff

Reviewed on Feb 12, 2026

River City Casino & Hotel
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
2801 Fountain Pl Wildwood MO
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $114 total per night from Feb 16 to Feb 17
$114 total
Feb 16 - Feb 17
Total with taxes and fees
9.2/10 Wonderful! (1,626 reviews)
Great room and friendly staff in a nice area. Will come again.

Reviewed on Feb 11, 2026

The Wildwood Hotel
See all 272 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
3,100
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Villa Antonio Winery, Persimmon Ridge Winery and Victoria Glaces Conservation Area Trailhead

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Frequently asked questions

How much does a Hillsboro vacation package cost?
You can pick up a vacation package to this top destination from $271 on Expedia. However, how much your vacation to Hillsboro costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Hillsboro?
If you're hoping to book a cheap Hillsboro vacation package, consider planning a trip in December, January and February. You'll generally find better rates on hotels and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Hillsboro?
The ideal duration for your Hillsboro vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to visit all the major sights and explore some hidden treasures along the way.
How to find the best Hillsboro package deals?
Begin your search for a Hillsboro package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Hillsboro package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Hillsboro adventure off to a flying start.
Is it cheaper to book a Hillsboro vacation as a package?
You can enjoy significant savings on your Hillsboro break by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Hillsboro?
If you've got your Hillsboro vacation dates locked in, book as early as you can to bag some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Hillsboro vacation packages?
Set off on your perfect trip to Hillsboro with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stick to your budget and snag great deals before they sell out.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.