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Highland Square Vacations from $274

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Your Highland Square Vacation

Highland Square is calling your name! Whatever type of adventure you're organizing, you can discover more of this neighborhood with a Highland Square vacation package. Your trip to Highland Square wouldn't be complete without stopping by major attractions nearby such as Stan Hywet Hall and Gardens, Akron Art Museum and University of Akron. Don't just wish for it — take action! Book your perfect Highland Square vacation with Expedia and experience travel your way.

The Latest Highland Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A breakfast bar with a chalkboard menu, kitchen appliances, and a sign indicating breakfast starts here.
    Jan 22 - Jan 24

    Hampton Inn Medina + Flight

    Medina
    2 nights
    2.5 star property
    8.8/10 - Excellent (1,006 reviews)
    Roundtrip • Orlando (MCO) - Akron (CAK)
    MCO - CAK • Nonstop CAK - MCO • Nonstop
    $302
    $274
    per traveler
    found 1 day ago
    Hampton Inn Medina
  • A buffet with various food items and a glass railing.
    Jan 22 - Jan 24

    DoubleTree by Hilton Akron Fairlawn + Flight

    Akron
    2 nights
    3.0 star property
    8.6/10 - Excellent (861 reviews)
    Roundtrip • Orlando (MCO) - Akron (CAK)
    MCO - CAK • Nonstop CAK - MCO • Nonstop
    $402
    $349
    per traveler
    found 1 day ago
    DoubleTree by Hilton Akron Fairlawn
  • A large bed with a wooden headboard, two bedside tables with lamps, and a light-colored floor.
    Dec 17 - Dec 22

    Super 8 by Wyndham Richfield/Cleveland + Flight

    Richfield
    5 nights
    2.0 star property
    5.0/10 - (1,000 reviews)
    Roundtrip • Atlanta (ATL) - Akron (CAK)
    ATL - CLE • Nonstop CLE - ATL • 1 stop
    $351
    $313
    per traveler
    found 23 hours ago
    Super 8 by Wyndham Richfield/Cleveland
  • A hotel bathroom with a large mirror, two sinks, a bathtub, and a flat-screen TV mounted on the wall.
    Jan 22 - Jan 24

    Best Western Plus North Canton Inn & Suites + Flight

    North Canton
    2 nights
    2.5 star property
    8.8/10 - Excellent (1,002 reviews)
    "Clean"
    Reviewed November 10, 2026
    Roundtrip • Orlando (MCO) - Akron (CAK)
    MCO - CAK • Nonstop CAK - MCO • Nonstop
    $310
    $279
    per traveler
    found 1 day ago
    Best Western Plus North Canton Inn & Suites
  • A modern interior with a checkered floor, a glass ceiling, and a staircase leading to a window.
    Jan 22 - Jan 24

    Bertram Inn at Glenmoor + Flight

    Canton
    2 nights
    3.5 star property
    8.6/10 - Excellent (332 reviews)
    Roundtrip • Orlando (MCO) - Akron (CAK)
    MCO - CAK • Nonstop CAK - MCO • Nonstop
    $304
    $275
    per traveler
    found 1 day ago
    Bertram Inn at Glenmoor

Where to stay in Highland Square

Find the best Highland Square areas and neighborhoods for the activities you enjoy most. Learn more about Highland Square
Learn more about Highland Square
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.
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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."
$99 nightly
The price is $99
Dec 6 - Dec 7
Total with taxes and fees
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.