Hillsboro Vacations from $336

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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.
AC Hotel by Marriott St. Louis Chesterfield

AC Hotel by Marriott St. Louis Chesterfield

3.5 out of 5
Price was $397, price is now $336 per person
$336
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
9.2/10 Wonderful! (224 reviews)
Staff was super friendly and welcoming. This was a last minute stay that I wish could have lasted longer. Clean rooms and great service.

Reviewed on Dec 28, 2025

The West End

The West End

2 out of 5
Central West End
Price was $519, price is now $431 per person
$431
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to St. Louis (STL)
8.4/10 Very Good! (389 reviews)
Great staff and management. Very helpful and fully responsive

Reviewed on Dec 25, 2025

The Cheshire

The Cheshire

4 out of 5
Price was $757, price is now $636 per person
$636
per person
Feb 20 - Feb 23
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
Very friendly staff. Clean, comfortable, and a GREAT breakfast!

Reviewed on Dec 28, 2025

Four Seasons Hotel St Louis

Four Seasons Hotel St Louis

5 out of 5
Downtown St. Louis
Price was $1,012, price is now $851 per person
$851
per person
Mar 15 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to St. Louis (STL)
9.4/10 Exceptional! (1,001 reviews)
Everything exceeded my expectations from the welcoming staff to the luxuriously appointed room, to the 4 feet deep bathtub in which to soak my cares away--it was a total dream come true. I would come back in a heartbeat at this home away from home.

Reviewed on Dec 13, 2025

St. Louis Union Station Hotel, Curio Collection by Hilton

St. Louis Union Station Hotel, Curio Collection by Hilton

4 out of 5
Downtown West
Price was $543, price is now $458 per person
$458
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
8.4/10 Very Good! (1,001 reviews)
The hotel proprty is huge and could benefit from better signage in various entryways and halls. Very disappointed in the lack of bartenders and wait staff in the Grand Ballroom after the IL vs MIZZOU Basketball game. From previous years management should know that there will be a large volume of fans that use the Ballroom as an after game drink space. Having three servers wait on over 300 people is ridiculous and an insult. Wait times for a drink were at least 30 minutes. Entirely disrespectful to fans and clients of the hotel.

Reviewed on Dec 28, 2025

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Discover the most popular places to visit in Hillsboro

Villa Antonio Winery

5/5(1 review)

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

4.5/5(4 reviews)

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
$85 nightly
The price is $98 total per night from Jan 4 to Jan 5
$98 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
7.8/10 Good! (1,051 reviews)
Room was clean

Reviewed on Dec 25, 2025

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

The Wildwood Hotel

3.5 out of 5
2801 Fountain Pl Wildwood MO
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $111 total per night from Jan 4 to Jan 5
$111 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,609 reviews)
Easy check-in, nice room, clean, charming furniture, and lovely lobby to sit and relax. Morning breakfast was very good. Something for everyone. Unfortunately, we were woke up at midnight by the fire alarm. Had to evacuate the hotel. And stand outside for about 30 minutes. They gave us the all clear, ...

Reviewed on Dec 25, 2025

The Wildwood Hotel
Best Western St. Louis-Kirkwood Route 66

Best Western St. Louis-Kirkwood Route 66

3.5 out of 5
1200 S Kirkwood Road Kirkwood MO
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $110 total per night from Jan 4 to Jan 5
$110 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.2/10 Very Good! (1,370 reviews)
Our stay was quiet and comfortable. Only a well used slightly stained bathtub kept this review from being excellent.

Reviewed on Dec 24, 2025

Best Western St. Louis-Kirkwood Route 66
See all 264 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 $336 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.