Highland County Vacation Packages

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Your Highland County Vacation

Reserve a vacation package to Highland County and make travel planning a breeze. With all the details organized before you leave, you can focus on enjoying every second in this amazing destination. A trip to Highland County offers so much to see and do. Not sure where to kick off your itinerary? Hillsboro is a leading place to stay here. Expedia has flights, hotels, car rentals and more to help you organize your own customized Highland County vacation today.

Top Highland County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Summit Hotel

The Summit Hotel

4 out of 5
Price was CA $1,241, price is now CA $1,031 per person
CA $1,031
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
9.2/10 Wonderful! (1,000 reviews)
We were in there for the Cincinnati Open championship weekend. This hotel is an official Cincinnati open hotel where many players were staying. Very well maintained but looked a little quiet. The occupancy might be very low. The restaurants in the property were closed for special events mostly probably for the Cincinnati Open. Overall good hotel.

Reviewed on Aug. 18, 2025

Hilton Cincinnati Netherland Plaza

Hilton Cincinnati Netherland Plaza

4 out of 5
Downtown Cincinnati
Price was CA $1,669, price is now CA $1,178 per person
CA $1,178
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
7.8/10 Good! (1,145 reviews)
Great old hotel. The building itself is beautiful old architecture but the age shows. Hallway carpets need to be cleaned, but overall a pleasant stay.

Reviewed on Aug. 26, 2025

Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
Price was CA $2,299, price is now CA $1,675 per person
CA $1,675
per person
Oct 10 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cincinnati (CVG)
8.4/10 Very Good! (1,000 reviews)
Enjoyed everything except the bathroom. No vent fan in the bathroom. Steamed up badly when showering. Service was good at the bar in the Stadium Sports Bar but it was very slow if seated at a table.

Reviewed on Aug. 26, 2025

Holiday Inn Express Hotel & Suites Richwood-Cincinnati South by IHG

Holiday Inn Express Hotel & Suites Richwood-Cincinnati South by IHG

2.5 out of 5
Price was CA $2,042, price is now CA $1,517 per person
CA $1,517
per person
Oct 10 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cincinnati (CVG)
8.8/10 Excellent! (1,006 reviews)
Nice property they have nice facilities the people were ok they wouldn’t let my door dasher deliver my food

Reviewed on Aug. 24, 2025

Pickle Factory Hotel

Pickle Factory Hotel

2.5 out of 5
Price was CA $1,188, price is now CA $1,033 per person
CA $1,033
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
9.4/10 Exceptional! (56 reviews)
It was VERY hard to find, but now that I know where it is, I will be staying again!

Reviewed on May 30, 2025

Highland County Hotel Deals

Days Inn by Wyndham Hillsboro

Days Inn by Wyndham Hillsboro

2.5 out of 5
103 Harry Sauner Rd, Hillsboro, OH
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Sep 6 to Sep 7
CA $133
CA $146 total
Sep 6 - Sep 7
includes taxes & fees
7/10 Good! (257 reviews)
"Very nice comfortable room and friendly staff"

Reviewed on Aug. 21, 2025

Days Inn by Wyndham Hillsboro
Paragon Inn Hillsboro

Paragon Inn Hillsboro

2 out of 5
883 W Main St, Hillsboro, OH
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Sep 6 to Sep 7
CA $94
CA $104 total
Sep 6 - Sep 7
includes taxes & fees
7.6/10 Good! (181 reviews)
"Staff very friendly and gave me a room with a walk in shower I really liked that."

Reviewed on Aug. 8, 2025

Paragon Inn Hillsboro
Hillsboro Inn & Suites

Hillsboro Inn & Suites

2 out of 5
838 West Main Street, Hillsboro, OH
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Sep 10 to Sep 11
CA $99
CA $109 total
Sep 10 - Sep 11
includes taxes & fees
6/10 (34 reviews)
"It’s at the end of town. Nothing in walking distance. No remote for tv. No coffee in room or on property! And the shampoo and soap dispensers were EMPTY!! Will not be back!"

Reviewed on Jun. 25, 2025

Hillsboro Inn & Suites
See all 231 properties in Highland County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Highland County vacation package cost?
The most affordable Highland County vacation package is CA $1,031, so the trip of your dreams can become a reality — without spending a fortune. Combine flights, hotels and car rentals to tailor a package that fits you.
How do I get a cheap travel package to Highland County?
Book everything in one place with our Highland County vacation packages. You'll find deals on hotels, flights and more that'll keep your pocket happy and your adventurousness alive. And, with more than 550 air carriers and 1,000,000 hotels worldwide to choose from, you'll have the flexibility to mix and match your own way.
What are the top hotels in Highland County?
For hotels in Hillsboro with comfy beds and friendly service, look up Days Inn by Wyndham Hillsboro and Greystone Motel. If you're visiting Leesburg as well, you can look forward to a solid night's sleep at Paragon Inn Hillsboro or Cedar Hill Motel.
How far in advance should I book my Highland County vacation?
To score discount prices, book nice and early. Airlines usually release flights, along with some of the lowest fares, nearly 12 months in advance. Hotels, experiences and car rental should also be booked well in advance so you can have the pick of the bunch. If you've decided on a last-minute getaway to Highland County, there are always lots of great deals on Expedia. Book something in today!
What does an Expedia Highland County travel package include?
That's up to you. You can choose from a variety of Highland County packages, such as a hotel, rental car and flight. You can also book a hotel and a flight, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like activities and experiences. Whatever your Highland County getaway looks like, get ready to save!
What should I know before booking a Highland County travel package?
Bundling your bookings into a Highland County vacation package is the easiest way to organize your trip. Not only that, you'll get great discounts when you combine your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Highland County Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You get to decide. We have access to more than 550 airline partners throughout the world, so you have lots of choice when planning your Highland County escape.
If I'm not able to travel, can I cancel my Highland County vacation package?
Yes, you can. We get that things don't always go to plan, so we're happy to help if you need to make changes to your Highland County vacation package. It may be possible to change or cancel your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Look up our Customer Service Portal for further information. Also, check your itinerary for the nitty-gritty on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.