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Highland Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Highland Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern kitchen with a wooden countertop, a built-in sink, and a patterned sofa.
    Dec 11 - Dec 14

    Motel 6 Streetsboro, OH + Flight

    Streetsboro
    3 nights
    2.0 star property
    7.2/10 - Good (1,004 reviews)
    Roundtrip • Vancouver (YVR) - Akron (CAK)
    YVR - CLE • 1 stop CLE - YVR • 1 stop
    CA $657
    CA $621
    per traveller
    found 14 hours ago
    Motel 6 Streetsboro, OH
  • A glass enclosure with a fire display, a red umbrella, and a brick wall with windows.
    Dec 9 - Dec 14

    Home2 Suites by Hilton Stow + Flight

    Stow
    5 nights
    3.0 star property
    9.2/10 - Wonderful (859 reviews)
    Roundtrip • Toronto (YYZ) - Akron (CAK)
    YYZ - CAK • 1 stop CAK - YYZ • 1 stop
    CA $1,675
    CA $1,488
    per traveller
    found 20 hours ago
    Home2 Suites by Hilton Stow
  • An indoor swimming pool with clear blue water, surrounded by white lounge chairs.
    Dec 9 - Dec 14

    Wingate by Wyndham Canton/Hall of Fame + Flight

    Canton
    5 nights
    3.0 star property
    5.6/10 - (1,004 reviews)
    Roundtrip • Toronto (YYZ) - Akron (CAK)
    YYZ - CAK • 1 stop CAK - YYZ • 1 stop
    CA $1,219
    CA $1,144
    per traveller
    found 20 hours ago
    Wingate by Wyndham Canton/Hall of Fame
  • A modern living room with a blue sofa, wooden coffee table, and a staircase with wooden railings.
    Dec 11 - Dec 14

    Comfort Inn & Suites Cuyahoga Falls - Akron + Flight

    Cuyahoga Falls
    3 nights
    3.0 star property
    9.0/10 - Wonderful (1,050 reviews)
    Roundtrip • Vancouver (YVR) - Akron (CAK)
    YVR - CLE • 1 stop CLE - YVR • 1 stop
    CA $895
    CA $851
    per traveller
    found 14 hours ago
    Comfort Inn & Suites Cuyahoga Falls - Akron
  • A building entrance with a blue bench, two potted plants, and a clear glass door.
    Dec 11 - Dec 14

    Motel 6 Medina, OH - Cleveland + Flight

    Medina
    3 nights
    2.0 star property
    6.6/10 - (580 reviews)
    "Not bad for a sleep"
    Reviewed November 3, 2026
    Roundtrip • Vancouver (YVR) - Akron (CAK)
    YVR - CLE • 1 stop CLE - YVR • 1 stop
    CA $664
    CA $654
    per traveller
    found 14 hours ago
    Motel 6 Medina, OH - Cleveland

Where to stay in Highland Square

Find the best Highland Square areas and neighborhoods for the activities you enjoy most.
A cityscape with a prominent church with twin towers, surrounded by modern buildings and a sunset sky.

Downtown Akron

Downtown Akron is noteworthy for its restaurants, and you can make a stop at top attractions like Canal Park and EJ Thomas Hall.
A waterfall cascading over moss-covered rocks in a forested area with autumn leaves.

Elizabeth Park Valley

Elizabeth Park Valley might not have many top sights, but Akron Art Museum and Akron-Summit County Public Library are two attractions nearby that you can check out.
A waterfall cascading over rocks surrounded by lush green foliage.

West Akron

While visiting West Akron, you might make a stop by sights like Akron Zoo and Perkins Park.
A large brick building with a tower, arched entrance, and multiple windows.
Photo by Carey René
Open Photo by Carey René

Northwest Akron

While visiting Northwest Akron, you might make a stop by sights like Stan Hywet Hall and Gardens and Cuyahoga Valley National Park.

North Hill

North Hill might not have many top sights, but Akron Art Museum and Chapel Hill Mall are two attractions nearby that you can check out.

Discover the most popular places to visit in Highland Square

Dr. Bob's Home

9.4/10 (3 reviews)
You can spend time studying the exhibits at Dr. Bob's Home during your trip to Akron. Attend a sporting event or discover the beautiful waterfalls in this family-friendly area.
See properties

Highland Square Hotel Deals

A hot tub under a wooden structure with a safety sign, a clock, and a grill in the background.

Berrodin Bed & Breakfast

Berrodin Bed & Breakfast
3.0 star property
Highland Square
9.2 out of 10, Wonderful, (119 reviews)
"Louis was a great host. We really enjoyed the information he gave us regarding things to do around the area. He was quick to respond to any questions we had. I would definitely recommend this bed and breakfast."
The price is CA $152
CA $152 total
includes taxes & fees
Nov 29 - Nov 30
Berrodin Bed & Breakfast
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.
See all properties in Highland Square

Frequently Asked Questions

How much does a Highland Square vacation package cost?

Get your credit card ready, because a getaway to Highland Square starts from a tempting CA $621. When you combine your flights, hotels and car rentals into a travel package, you'll score the best deals.

How do I get a cheap travel package to Highland Square?

Book everything in the one place with our Highland Square vacation packages. You'll find deals on flights, hotels, tours and more that'll keep your credit card happy and your adventurous spirit full. And, with more than 550 air carriers and 1,000,000 properties across the globe to select from, you'll have the flexibility to mix and match as you want.

Where should I stay in Highland Square?

A trip to Highland Square has to include Stan Hywet Hall and Gardens and Firestone Country Club. Stay somewhere close by for easy access to these famous tourist attractions.

What are the top hotels in Highland Square?

Berrodin Bed And Breakfast is one of Highland Square's most popular properties. Book a room here and you'll be able to snooze soundly knowing you're in good hands.

How far in advance should I book my Highland Square vacation?

It all depends on the airline, but it's usually possible to compare international fares on Expedia nearly a year in advance. While it's advisable to book ahead of time, lucky customers occasionally score a cheaper ticket only weeks before the date of departure.

What does an Expedia Highland Square travel package include?

Hotels, flights and car rentals — we connect you to the very best bargains. All you have to do is select your preferred combination. Once you've made your booking, you can add on the exciting stuff like sightseeing activities. Our travel packages make it simple to craft an exciting Highland Square trip.

What should I know before booking a Highland Square travel package?

Bundling your bookings into a Highland Square vacation package is the most convenient way to organize your trip. Not only that, you'll save big just for combining your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?

Can I choose my airline with a Highland Square Expedia vacation package?

You can. Expedia has access to more than 550 airline partners across the globe, so fly with the carrier that's a good fit for your travel needs.

If I'm not able to travel, can I cancel my Highland Square vacation package?

If your vacation plans in Highland Square have been upended, it's comforting to know that it's possible to amend or cancel your booking. If you booked less than 24 hours ago, you may be able to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose fees. To find out more, check our Customer Service Portal.

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