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.
Crowne Plaza Cleveland Airport by IHG

Crowne Plaza Cleveland Airport by IHG

3.5 out of 5
per person
Sep 23 - Sep 26
found 6 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Cleveland (CLE)
7.6/10 Good! (1,000 reviews)
Paid for a balcony room but there were no available. They told me that Expedia should not sold it to me and I should take it up with them.

Reviewed on Jul. 6, 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
per person
Sep 23 - Sep 26
found 6 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Cleveland (CLE)
8.6/10 Excellent! (1,442 reviews)
Great place to stay and friendly staff

Reviewed on Jul. 13, 2025

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
per person
Sep 23 - Sep 26
found 6 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Cleveland (CLE)
9/10 Wonderful! (812 reviews)
Lobby was nice. Room ok Maids never came to clean room Toilet wouldn’t flush until maintenance came to fix

Reviewed on Jun. 23, 2025

The Ritz-Carlton, Cleveland

The Ritz-Carlton, Cleveland

5 out of 5
Downtown Cleveland
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Cleveland (CLE)
8.8/10 Excellent! (260 reviews)
The walk thru tunnel to see the Cavs

Reviewed on May 7, 2025

Hilton Cleveland Downtown

Hilton Cleveland Downtown

4 out of 5
Downtown Cleveland
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Cleveland (CLE)
9.2/10 Wonderful! (1,064 reviews)
Awesome hotel, exceeded expectations in every way. Would highly recommend & also will be looking to stay here in future visits.

Reviewed on Jul. 11, 2025

Ready to book your vacation to Highland Hills?

 

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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
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! (1,447 reviews)
Great trip
"Everything was amazing."

Reviewed on Jul. 11, 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! (1,209 reviews)
"Like the courtyard even though some construction tape was up. It was a great space for us to play games instead of being cramped in our rooms. The rooms were nice and clean overall. I was not to fond of the elevator not having any air as it took a while for it to get to each floor. On those hot days, ..."

Reviewed on Jul. 12, 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 $115 per night from Jul 20 to Jul 21
CA $115
CA $135 total
Jul 20 - Jul 21
includes taxes & fees
7.2/10 Good! (1,005 reviews)
Greatstay
"It wss a great hotel loved it"

Reviewed on Jul. 10, 2025

Best Western Plus Strongsville Cleveland
See all 1,693 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Highland Hills

Huntington Bank Field

Huntington Bank Field

4.5/5(38 reviews)

Catch an event at Huntington Bank Field during your trip to Cleveland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Huntington Bank Field
Progressive Field

Progressive Field

4.5/5(44 reviews)

Catch an event at Progressive Field during your trip to Cleveland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Progressive Field
Rock and Roll Hall of Fame featuring interior views and music

Rock and Roll Hall of Fame

4.5/5(117 reviews)

Discover the music and memorabilia from the greatest rock bands in the world and find out why Cleveland is so important to the world of Rock and Roll.

Rock and Roll Hall of Fame

What to do in Highland Hills

Cleveland: Eerie Ghosts Haunted Walking Tour

Phantom's Parade on Prospect: Cleveland Ghost Tours

CA $33
per adult
Phantom's Parade on Prospect: Cleveland Ghost Tours
Bridalveil falls

Cuyahoga Valley National Park Self-Guided Audio Tour

CA $21
per traveller
Cuyahoga Valley National Park Self-Guided Audio Tour
Guests smiling & waving as we tour Cleveland.

Cleveland Comedy City Tour

CA $54
per adult
Cleveland Comedy City Tour
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 $940 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.