Highland Hills Vacation Packages

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    Better together

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

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Your Highland Hills Vacation

Say bye-bye to planning hassles and hello to a Highland Hills vacation package. With your travel details organized before you leave, you can focus on discovering every inch of this city, starting with The Flats, which is great for cycling, distilleries and craft breweries and cafes. Eager to explore your new surroundings? Case Western Reserve University, Legacy Village and Pinecrest Plaza Shopping are among the top-rated places to visit during a trip to Highland Hills. Stop daydreaming and start adventuring. Explore the broad range of options on Expedia today and put your Highland Hills vacation plans into action!

Top Highland Hills Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn by Wyndham Sandusky near Cedar Point
The Inn at Fulton
Cedar Stables Inn and Suites
The Washington Boutique Hotel
Days Inn by Wyndham Sandusky / Cedar Point

Ready to book your vacation to Highland Hills?

 

Choose your dates

Highland Hills Hotel Deals

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
777 Saint Clair Ave Ne, Cleveland, OH
The price is CA $204 per night from Jul 31 to Aug 1
CA $204
CA $240 total
Jul 31 - Aug 1
includes taxes & fees
8.4/10 Very Good! (1,454 reviews)
Anniversary stay
"We booked through hotels.com for our stay for our anniversary. When we checked in, we were told that we couldn’t have a king bed (which is what we booked) but they upgraded us to a corner suite. The suite was spacious but a bit worn out. The bathroom was also not very clean."

Reviewed on Jul. 13, 2025

The Westin Cleveland Downtown
Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
651 Huron Rd E, Cleveland, OH
Fully refundable
The price is CA $152 per night from Aug 4 to Aug 5
CA $152
CA $179 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very Good! (1,220 reviews)
"The only complaint that we have is that the water pressure in the show was bad - other than that Excellent!"

Reviewed on Jul. 14, 2025

Hotel Indigo Cleveland Downtown by IHG
Best Western Plus Strongsville Cleveland

Best Western Plus Strongsville Cleveland

3 out of 5
15471 Royalton Rd, Strongsville, OH
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Jul 20 to Jul 21
CA $92
CA $108 total
Jul 20 - Jul 21
includes taxes & fees
7.2/10 Good! (1,015 reviews)
"Please fix your WiFi, rest is all good."

Reviewed on Jul. 14, 2025

Best Western Plus Strongsville Cleveland
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.

Discover the most popular places to visit in Highland Hills

What to do in Highland Hills

Frequently asked questions

How much does a Highland Hills vacation package cost?
Offering great value package deals from CA $1,032 on Expedia, you'll be surprised at how little a vacation to Highland Hills costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Highland Hills?
January, February and November are the best times to look for cheap Highland Hills vacation packages. Opting to travel in quieter periods means you'll typically find better prices on accommodations and flights.
How many days is enough for Highland Hills?
With around 2 days, you'll have plenty of time to experience popular neighbourhoods such as University Circle and Orange during your Highland Hills vacation. Make sure to also add ETON Chagrin Blvd Shopping Centre and Freeway Lanes to your list of must-sees. Looking for more adventures? Consider venturing outside of Highland Hills on day trips and tours.
How to find the best Highland Hills package deals?
Start your search for a Highland Hills package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," 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 Highland Hills package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Highland Hills adventure underway.
Is it cheaper to book a Highland Hills vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Highland Hills vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Highland Hills?
If you've got your Highland Hills travel dates confirmed, book as early as you can to score some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Highland Hills?

  1. Choose your dates: The things you want to do in Highland Hills and your favourite season can help you decide when to go.
  2. Set your budget: Factor in costs such as flights, transportation and food when calculating how much to save for your trip to Highland Hills. Then, choose a property that fits your budget, whether that's an affordable stay or a deluxe retreat.
  3. Decide how long to go for: Now that you're more familiar with Highland Hills, you can figure out the right length of your vacation. Put together a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Highland Hills vacation package that brings all your bookings together.

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