Highland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Highland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Englewood Dayton Airport

Days Inn by Wyndham Englewood Dayton Airport

2 out of 5
Price was CA $1,006, price is now CA $852 per person
CA $852
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Dayton (DAY)
8.4/10 Very good! (1,564 reviews)
The A/C did not do an adequate job in cooling the room. Set the A/C to 65 and the room did not get cold. Maybe around 75. There was no fullsize towels. Only to find out that the shower would not turn on. The front desk said that I probably did not turn the shower on properly.

Reviewed on Jul 8, 2026

Graduate by Hilton Columbus

Graduate by Hilton Columbus

4 out of 5
Downtown Columbus
Price was CA $1,843, price is now CA $1,523 per person
CA $1,523
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Columbus (CMH)
9.2/10 Wonderful! (1,007 reviews)
The property was clean and safe. The beds are very low to the ground and pretty soft so it is kind of comical to get in and out of the bed. The room is generally pretty dark. There are also a lack of outlets in the room.. so plugging in a laptop or phone isn't exactly easy. The coffee in the room is instant coffee which ok, but to plug in the kettle is a total hassle.

Reviewed on Jul 8, 2026

Jungle House Luxury Stays - Downtown Chillicothe

Jungle House Luxury Stays - Downtown Chillicothe

5 out of 5
Price was CA $1,545, price is now CA $1,297 per person
CA $1,297
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Columbus (CMH)
9.6/10 Exceptional! (14 reviews)
Very clean, roomy, comfy beds. Walk of .5 mile to downtown area and plenty of parking

Reviewed on Jun 16, 2026

The Hotel@Dayton South

The Hotel@Dayton South

2.5 out of 5
Price was CA $1,018, price is now CA $870 per person
CA $870
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Dayton (DAY)
8.4/10 Very good! (1,015 reviews)
Plenty of parking, with spaces close to the entrance. Noisey people outside late at night two nights in a row. TV pretty much useless.

Reviewed on Jul 8, 2026

Super 8 by Wyndham Gallipolis Pt Pleasant Area

Super 8 by Wyndham Gallipolis Pt Pleasant Area

2 out of 5
Price was CA $1,106, price is now CA $970 per person
CA $970
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Columbus (CMH)
8/10 Very good! (1,008 reviews)
The staff stated the pool was “ under maintenance “. The pool was green. We were told to visit another hotel to swim in their pool, which is not accommodating at all. We were very disappointed because we picked this hotel because of the location for the Moth man and the pool. The hotel is desperately in need of updating. Walking on the floors in our hotel room our feet became back from the dirt. The mini fridge was leaking water. Breakfast was mediocre no hot food.

Reviewed on Jul 7, 2026

Ready to book your vacation to Highland?

 

Choose your dates

Highland Hotel Deals

Royalton Inn and Suites Wilmington

Royalton Inn and Suites Wilmington

2 out of 5
201 Carrie Dr Wilmington OH
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Jul 11 to Jul 12
CA $132
CA $149 total
Jul 11 - Jul 12
includes taxes & fees
7.2/10 Good! (420 reviews)
"The room was clean and nice. Exterior side door not secure. Hallways were weren't air conditioned and public areas not very clean. Staff does not speak English very well. Hard to communicate."

Reviewed on Jul 2, 2026

Royalton Inn and Suites Wilmington
Holiday Inn Wilmington by IHG

Holiday Inn Wilmington by IHG

3 out of 5
123 Gano Rd Wilmington OH
Fully refundable
The price is CA $191 per night from Jul 26 to Jul 27
CA $191
CA $224 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (680 reviews)
"Very nice facility."

Reviewed on Jun 30, 2026

Holiday Inn Wilmington by IHG
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 $117 per night from Jul 16 to Jul 17
CA $117
CA $129 total
Jul 16 - Jul 17
includes taxes & fees
7.8/10 Good! (225 reviews)
"Good place to sleep while passing through. Several miles off the interstate. No staff were available at checkout."

Reviewed on Jun 19, 2026

Paragon Inn Hillsboro
See all 126 properties in Highland
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 vacation package cost?
Offering excellent value package deals from CA $852 on Expedia, you'll be pleasantly surprised at how much a vacation to Highland costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Highland?
If you're looking to book a cheap Highland vacation package, consider planning a trip in January, February and March. You'll generally find better rates on hotels and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Highland?
Typically, a handful of days is enough to tick off the top attractions during your Highland vacation. But if you prefer to have more time to kick back or take day trips, consider extending your itinerary.
How to find the best Highland package deals?
Bagging a cheap Highland package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Highland package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Highland vacation as a package?
You can enjoy significant savings on your Highland escape by booking a tailored 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 Highland?
If you're considering a spontaneous Highland getaway, check out 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 incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Highland?

  1. Pick your dates: What you want to do in Highland and your favourite season will help you decide when to travel.
  2. Plan your budget wisely: On top of the price of your stay, you should consider other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Highland.
  3. Decide how long to go away for: Now that you know more about Highland, you can figure out the right length of your break. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Highland vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.