Highland County Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.
Jungle House Urban Lofts - Short North & Convention Center

Jungle House Urban Lofts - Short North & Convention Center

5 out of 5
Downtown Columbus
Price was CA $1,178, price is now CA $980 per person
CA $980
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Columbus (CMH)
8.6/10 Excellent! (12 reviews)
Great location! Eight minute walk to Convention Center. Loved all the plants! So cozy! Hosts very attentive and friendly. Will definitely be coming back!

Reviewed on Mar 2, 2026

voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

4 out of 5
Downtown Cincinnati
Price was CA $1,639, price is now CA $1,252 per person
CA $1,252
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
9.2/10 Wonderful! (1,101 reviews)
Room was just okay. It was not very clean. Had crusty stains on the chair covered by a pillow and crust on the bathroom door. There were not any disposable cups, only glass, which is not very sanitary. The ice machine also did not work. I had to go to a different floor. Staff were very nice the restaurant was Amazing! Espresso martini was delicious. Close proximity (walking distance) to Hard Rock Casino.

Reviewed on Mar 1, 2026

Hotel Covington Cincinnati Riverfront

Hotel Covington Cincinnati Riverfront

4 out of 5
Price was CA $1,804, price is now CA $1,402 per person
CA $1,402
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
9.6/10 Exceptional! (1,002 reviews)
Amazing property. Great staff wonderful bar and restaurant. Beautiful you can’t go wrong booking here.

Reviewed on Mar 2, 2026

Embassy Suites by Hilton Cincinnati RiverCenter

Embassy Suites by Hilton Cincinnati RiverCenter

3.5 out of 5
Price was CA $1,393, price is now CA $1,100 per person
CA $1,100
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cincinnati (CVG)
7.4/10 Good! (1,005 reviews)
The room was comfortable.. Front desk staff friendly.. nice to have a free glass of wine

Reviewed on Mar 1, 2026

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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 Apr 3 to Apr 4
CA $133
CA $147 total
Apr 3 - Apr 4
includes taxes & fees
7.2/10 Good! (288 reviews)
Good room staff was very helpful. Nice place to stay!

Reviewed on Feb 20, 2026

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 $107 per night from Mar 6 to Mar 7
CA $107
CA $119 total
Mar 6 - Mar 7
includes taxes & fees
7.8/10 Good! (203 reviews)
Clean room helpful staff

Reviewed on Feb 2, 2026

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 $98 per night from Mar 4 to Mar 5
CA $98
CA $108 total
Mar 4 - Mar 5
includes taxes & fees
6.6/10 (42 reviews)
Room was clean , recently redone

Reviewed on Feb 27, 2026

Hillsboro Inn & Suites
See all 236 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 $980, 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.