Hillsboro Vacations from $319
Book a Hotel + Flight or Car together to unlock savings
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 Cheshire
$474
per person
Dec 3 - Dec 7
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
The staff, lobby, breakfast were all good. The room was mid-tier, however. Not bad, but still a bit pricey for what it was.
Reviewed on Sep 28, 2026
Stay near popular Hillsboro attractions
Lake Trails
Commune with nature and explore the great outdoors at Lake Trails during your travels in Hillsboro. Amble around the area's parks or visit its monuments.
Villa Antonio Winery
7.2/10 (5 reviews)
This Italian-inspired vineyard pairs award-winning wines with wood-fired pizzas in a serene lakeside setting. Enjoy weekend live music on the expansive outdoor patio while sampling both house wines and craft beers.
Sandy Creek Covered Bridge State Historic Site
8.6/10 (4 reviews)
This historic red bridge, built in 1872, showcases the rare Howe-truss design as one of Missouri's last four covered bridges. Stroll through its 74-foot span and enjoy a picnic in the serene surrounding park.
Cole Lake
This serene 39-acre private lake offers residents a peaceful retreat with personal docks and stocked waters. Accessible only to homeowners and guests, Cole Lake exemplifies exclusive lakeside living in Valle Township.
Daley Lake
Daley Lake offers a serene retreat in rural Missouri with peaceful shorelines and natural surroundings. Bring a camera to capture the tranquil landscape and pack essentials for a self-sufficient visit.
Lake Lorraine
Lake Lorraine offers a peaceful retreat with pristine waters surrounded by Missouri's lush greenery. Bring fishing gear and a picnic to fully experience this tranquil natural escape.
Lindwell Lake
Lindwell Lake offers tranquil lakefront views in a private setting near Hillsboro, Missouri. Remember that access is restricted to property owners and their guests only.
Sunridge Park
Sunridge Park offers a tranquil 4.5-acre escape with a playground, picnic pavilion, and observation tower for panoramic views. Climb the tower in fall to witness spectacular foliage colors across the Hillsboro landscape.
Hillsboro Hotel Deals
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham
1088 South Highway Drive Fenton MO
Fully refundableReserve now, pay when you stay
$94 nightly
$109 total
Sep 29 - Sep 30
Total with taxes and fees
7.8/10 Good! (1,577 reviews)
"I traveled with my family and we rest really well 2 nights"
Reviewed on Sep 28, 2026
River City Casino & Hotel
777 River City Casino Blvd St. Louis MO
Fully refundableReserve now, pay when you stay
$110 nightly
$129 total
Oct 15 - Oct 16
Total with taxes and fees
9/10 Wonderful! (1,806 reviews)
"Nice room Helpful staff Would stay again"
Reviewed on Sep 28, 2026
Best Western St. Louis Inn
6224 Heimos Industrial Park Dr St. Louis MO
Fully refundableReserve now, pay when you stay
$75 nightly
$86 total
Oct 6 - Oct 7
Total with taxes and fees
8.4/10 Very Good! (1,162 reviews)
"Very nice rooms. And looks to be freshly remodeled."
Reviewed on Sep 26, 2026
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 $319 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.