Highland Hills Vacation Packages

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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.
Cedar Point's Express Hotel

Cedar Point's Express Hotel

2 out of 5
Price was CA $1,109, price is now CA $957 per person
CA $957
per person
Aug 16 - Aug 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
8.6/10 Excellent! (1,130 reviews)
The rooms are nice. It’s worth it to have the early entry to Cedar Point. The pool seemed nice(didn’t use), but lots of seagulls around. Located right by Dairy Queen and Mcdonalds for quick bites.

Reviewed on Jul 8, 2026

Hotel Kilbourne Downtown Sandusky

Hotel Kilbourne Downtown Sandusky

2.5 out of 5
Historic Downtown Sandusky
Price was CA $1,634, price is now CA $1,338 per person
CA $1,338
per person
Aug 16 - Aug 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
9/10 Wonderful! (708 reviews)
The location of the hotel is perfect for walking to restaurants or just taking a stroll through downtown. Our room was clean and very well decorated. While having a waterfall shower was great, there was only a partial glass wall and no shower door, so naturally when you shower there for is getting extremely wet. I would recommend bringing your own snacks, because the snacks they provide in the room are very pricy. The staff was super friendly!!

Reviewed on Jul 2, 2026

Quality Lodge

Quality Lodge

2.5 out of 5
Price was CA $1,181, price is now CA $979 per person
CA $979
per person
Aug 16 - Aug 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
7.8/10 Good! (347 reviews)
This area is nothing like the pictures, just was not what we were expecting.

Reviewed on Jun 14, 2026

Explorer Rest & Recreation

Explorer Rest & Recreation

2 out of 5
Price was CA $1,124, price is now CA $967 per person
CA $967
per person
Aug 16 - Aug 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
9.2/10 Wonderful! (394 reviews)
Had a little trouble checking in because we booked third party and didn’t get the instruction text. However we were next door to a very loud dog and the staff went above and beyond to allow us access to another room away from the dog if it was still barking at bedtime. Luckily it was not and quieted down when the people came back from dinner. But the offer was very appreciated. I also liked having 3 separate beds when traveling with teenagers. Thank you!

Reviewed on Jul 7, 2026

Cedar Stables Inn and Suites

Cedar Stables Inn and Suites

2.5 out of 5
Price was CA $1,213, price is now CA $1,046 per person
CA $1,046
per person
Aug 16 - Aug 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
8.8/10 Excellent! (526 reviews)
Checking in wasn't too bad once we figured out where to go. The shower stopped up the first night so I called the front desk and was told 'I will let maintenance know" We never saw them or heard from them. So the next morning, I let housekeeping know about it being stopped up again and was told again....I will let maintenance know. Still nothing from anyone. I wasnt even able to take a shower because it was not draining at all. After being at Cedar Point all day, you really need to be able to shower.

Reviewed on Jul 6, 2026

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Highland Hills Hotel Deals

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
777 Saint Clair Ave Ne Cleveland OH
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Jul 12 to Jul 13
CA $197
CA $231 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (74 reviews)
"very inviting staff, clean property and rooms"

Reviewed on Jul 9, 2026

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 $140 per night from Jul 26 to Jul 27
CA $140
CA $165 total
Jul 26 - Jul 27
includes taxes & fees
8.4/10 Very good! (1,777 reviews)
"Room Very"

Reviewed on Jul 9, 2026

Hotel Indigo Cleveland Downtown by IHG
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
1100 Carnegie Ave Cleveland OH
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jul 12 to Jul 13
CA $179
CA $211 total
Jul 12 - Jul 13
includes taxes & fees
7.6/10 Good! (1,010 reviews)
"Pool and hot tub were closed, sheets were too small for the bed. Toilet was running."

Reviewed on Jul 8, 2026

Hilton Garden Inn Cleveland Downtown
See all 1,856 properties in Highland Hills
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.
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What to do in Highland Hills

Cleveland: Eerie Ghosts Haunted Walking Tour

Phantom's Parade on Prospect: Cleveland Ghost Tours

CA $34
per adult
100% of travellers recommend
Phantom's Parade on Prospect: Cleveland Ghost Tours
Phantom's Parade on Prospect: Cleveland Ghost Tours

Phantom's Parade on Prospect: Cleveland Ghost Tours

CA $45
per adult
90% of travellers recommend
Phantom's Parade on Prospect: Cleveland Ghost Tours
Picture 3 for Activity Cleveland: Museum of Illusions Entry Ticket

Museum of Illusions Cleveland Entry Ticket

CA $48
per adult
100% of travellers recommend
Museum of Illusions Cleveland Entry Ticket
See all activities in Highland Hills

Frequently asked questions

How much does a Highland Hills vacation package cost?
Offering great value package deals from CA $957 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.

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.