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.
Wyndham Cleveland Airport

Wyndham Cleveland Airport

3.5 out of 5
Jefferson
Price was CA $976, price is now CA $885 per person
CA $885
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
6.4/10 (1,041 reviews)
The Hotel was good but could not find food very close

Reviewed on Sep. 5, 2025

Courtyard by Marriott Cleveland University Circle

Courtyard by Marriott Cleveland University Circle

3 out of 5
University Circle
Price was CA $1,406, price is now CA $1,270 per person
CA $1,270
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.8/10 Excellent! (931 reviews)
Valet parking was a disaster!!!

Reviewed on Aug. 19, 2025

Crowne Plaza Cleveland at Playhouse Square by IHG

Crowne Plaza Cleveland at Playhouse Square by IHG

3.5 out of 5
Downtown Cleveland
Price was CA $1,044, price is now CA $943 per person
CA $943
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.8/10 Excellent! (1,207 reviews)
Beautiful hotel. Staff very helpful and friendly. We had a beautiful view from our room. Lots of activities restaurants and shows within walking distance. Planning on going back next summer

Reviewed on Sep. 6, 2025

Courtyard by Marriott Cleveland Airport South

Courtyard by Marriott Cleveland Airport South

3 out of 5
Price was CA $976, price is now CA $908 per person
CA $908
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.2/10 Very Good! (1,002 reviews)
Cameron at the front desk is too notch!!!

Reviewed on Aug. 31, 2025

Residence Inn by Marriott Cleveland Independence

Residence Inn by Marriott Cleveland Independence

3 out of 5
Price was CA $963, price is now CA $898 per person
CA $898
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.4/10 Very Good! (976 reviews)
Staff is very nice & helpful. Rooms was clean. Surrounded by lots of restaurants & free way access. Plenty of parking. Great for extended stays

Reviewed on Sep. 4, 2025

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Highland Hills Hotel Deals

Ramada by Wyndham Cleveland Independence

Ramada by Wyndham Cleveland Independence

3.5 out of 5
5300 Rockside Road, Independence, OH
Fully refundableReserve now, pay when you stay
The price is CA $101 per night from Sep 11 to Sep 12
CA $101
CA $118 total
Sep 11 - Sep 12
includes taxes & fees
Ramada by Wyndham Cleveland Independence
The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
777 Saint Clair Ave Ne, Cleveland, OH
The price is CA $178 per night from Sep 28 to Sep 29
CA $178
CA $210 total
Sep 28 - Sep 29
includes taxes & fees
The Westin Cleveland Downtown
La Quinta Inn & Suites by Wyndham Cleveland - Airport North

La Quinta Inn & Suites by Wyndham Cleveland - Airport North

3 out of 5
4222 W 150th St, Cleveland, OH
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Sep 14 to Sep 15
CA $119
CA $140 total
Sep 14 - Sep 15
includes taxes & fees
La Quinta Inn & Suites by Wyndham Cleveland - Airport North
See all 1,716 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

Rock and Roll Hall of Fame featuring interior views and music

Rock and Roll Hall of Fame

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
Huntington Bank Field

Huntington Bank Field

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

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

What to do in Highland Hills

Cleveland: Eerie Ghosts Haunted Walking Tour

Phantom's Parade on Prospect: Cleveland Ghost Tours

CA $33
per adult
100% of travellers recommend
Phantom's Parade on Prospect: Cleveland Ghost Tours
Hear Haunted Histories on Our cleveland Ghost Tour.

Cleveland Ghosts Tour

CA $44
per adult
90% of travellers recommend
Cleveland Ghosts Tour
The Escape Game: Epic 60-Minute Adventures at Crocker Park

The Escape Game: Epic 60-Minute Adventures at Crocker Park

CA $58
per adult
100% of travellers recommend
The Escape Game: Epic 60-Minute Adventures at Crocker Park
See all activities in Highland Hills
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.