Hillsboro Vacations from $343

Book a Hotel + Flight or Car together to unlock savings

Your Hillsboro Vacation

Memorable adventures await when you lock in a Hillsboro vacation package. Whether you're a foodie, art buff or just a traveler who appreciates new places, there's something for everyone in this interesting city. Tuckahoe State Park, Museum of Rural Life and Adkins Arboretum are just some of the attractions you'll want to check out during your trip to Hillsboro. Expedia has what you need to escape your routine. Tailor your vacation to Hillsboro to match your travel style, whatever that may be!

The Latest Hillsboro vacation packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Washington D.C. – Convention Center
Beacon Hotel & Corporate Quarters
Lyle Washington D.C.
Hilton Washington DC Capitol Hill
Sofitel Washington DC Lafayette Square
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Hillsboro Hotel Deals

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3 out of 5
3206 Main St Grasonville MD
$103 nightly
The price is $115 total per night from Dec 21 to Dec 22
$115 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us.

Reviewed on Dec 7, 2025

Hilton Garden Inn Kent Island Marina
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 out of 5
3101 Main Street Grasonville MD
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $93 total per night from Dec 22 to Dec 23
$93 total
Dec 22 - Dec 23
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
Everything was just fine.

Reviewed on Nov 28, 2025

Best Western Kent Narrows Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
$517 nightly
The price is $568 total per night from Dec 14 to Dec 15
$568 total
Dec 14 - Dec 15
Total with taxes and fees
9.4/10 Exceptional! (370 reviews)
Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay.

Reviewed on Nov 12, 2025

Inn at Perry Cabin
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
Top Sights
Avalon Theatre, Martinak State Park and Historical Society of Talbot County

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Frequently asked questions

How much does a Hillsboro vacation package cost?
You can grab a vacation package to this popular destination from $343 on Expedia. But how much your vacation to Hillsboro costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Hillsboro?
If you're looking to book a cheap Hillsboro vacation package, consider visiting in January, June and November. You'll generally find better prices on flights and accommodations during these months — ideal for a budget-friendly break.
How many days is enough for Hillsboro?
Usually, a handful of days is enough to explore the top sights during your Hillsboro vacation. However, if you prefer to have more time to relax or take day tours, think about extending your itinerary.
How to find the best Hillsboro package deals?
Use Expedia's filter tool to find some tempting Hillsboro package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Hillsboro package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Hillsboro vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can personalize your Hillsboro trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Hillsboro?
If you're planning an impromptu Hillsboro getaway, 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 land sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Hillsboro vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Hillsboro trip across 3, 6 or 12 months. There are also no hidden 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.