Highland Hills Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Ariel Broadway Hotel
CA $1,226
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Cleveland (CLE)
8.2/10 Very good! (654 reviews)
Great location. Very friendly staff. Fantastic view from our corner room.
We had dinner on the rooftop and it was a great experience. The waitress was so nice and competent, handling a big party and the rest of the diners by herself. She did a fantastic job.
Reviewed on Aug 30, 2026
Crowne Plaza Cleveland at Playhouse Square by IHG
Downtown Cleveland
CA $1,459
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Cleveland (CLE)
9/10 Wonderful! (1,416 reviews)
Excellent hotel with outstanding amenities and a convenient downtown location. Friendly staff and a great restaurant. Highly recommend this property.
Reviewed on Sep 3, 2026
Ready to book your vacation to Highland Hills?
Highland Hills Hotel Deals
Best Western Plus Strongsville Cleveland
15471 Royalton Rd Strongsville OH
Fully refundableReserve now, pay when you stay
CA $92
CA $108 total
Oct 4 - Oct 5
includes taxes & fees
7.8/10 Good! (1,611 reviews)
"Everything is very good 👍"
Reviewed on Sep 3, 2026
Hotel Indigo Cleveland Downtown by IHG
651 Huron Rd E Cleveland OH
Fully refundable
CA $147
CA $173 total
Sep 20 - Sep 21
includes taxes & fees
The Westin Cleveland Downtown
777 Saint Clair Ave Ne Cleveland OH
Fully refundableReserve now, pay when you stay
CA $179
CA $210 total
Sep 6 - Sep 7
includes taxes & fees
8.6/10 Excellent! (279 reviews)
"Absolute perfection. Went for an anniversary and they upgraded my room - had an ocean view with an amazing sunset. Thank you so much guys it was beyond expectations"
Reviewed on Sep 3, 2026
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.
What to do in Highland Hills
Cleveland Guardians Baseball Game at Progressive Field
CA $81
per adult
Phantom's Parade on Prospect: Cleveland Ghost Tours
CA $33
per adult
100% of travellers recommend
Phantom's Parade on Prospect: Cleveland Ghost Tours
CA $36
per adult
90% of travellers recommend
Frequently asked questions
How much does a Highland Hills vacation package cost?
Offering great value package deals from CA $835 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?
- Choose your dates: The things you want to do in Highland Hills and your favourite season can help you decide when to go.
- 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.
- 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.
- 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.
