Highland Square Vacations from $523
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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.
DoubleTree by Hilton Akron Fairlawn
Price was $801, price is now $705 per person
$705
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Akron (CAK)
8.6/10 Excellent! (823 reviews)
The location was perfect. I needed a late checkout and they were very accommodating. We ate lunch at the restaurant and it was delicious. The menu had many tasty options, it was hard to decide. As usual, the cookie was perfect!
Reviewed on Jun 14, 2026
Holiday Inn Express Akron NW - Fairlawn by IHG
Price was $643, price is now $572 per person
$572
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Akron (CAK)
8.8/10 Excellent! (846 reviews)
Arrived late in the evening ready to relax and sleep for the night. After doing my usual inspection of the bed I discovered crumbs, stray hairs, and what looked like makeup on the pillow cases and sheets. The room was cleanish, about as clean as a typical hotel. It apps if they just didn’t change the sheets. I did mention to the front desk staff and they were friendly and helpful. Otherwise the stay was fine with no additional issues.
Reviewed on Jun 26, 2026
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
Downtown Akron
5 out of top 10 points of interest in this area
4/5(10 area reviews)
Downtown Akron is noteworthy for its restaurants, and you can make a stop at top attractions like Canal Park and EJ Thomas Hall.
Highland Square Hotel Deals
Berrodin Bed & Breakfast
814 Bloomfield Ave Akron OH
$113 nightly
The price is $113 total per night from Jun 29 to Jun 30
$113 total
Jun 29 - Jun 30
Total with taxes and fees
9.2/10 Wonderful! (116 reviews)
"The description of the B&B did not mention that the 3 rooms available would be sharing the 1 bathroom. The bathroom room was very nice though, and provided everything needed; shampoo, body soap, conditioner and towels. The bedroom was well appointed and the bed was extremely comfortable. The breakfast ..."
Reviewed on Jun 8, 2026
Courtyard by Marriott Canton
4375 Metro Cir Nw Canton OH
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $117 total per night from Jun 30 to Jul 1
$117 total
Jun 30 - Jul 1
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"So friendly"
Reviewed on Jun 26, 2026
The Aurora Inn
30 Shawnee Trail Aurora OH
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $103 total per night from Jul 5 to Jul 6
$103 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (697 reviews)
"Great stay, although short. Would love to come back and enjoy the courtyard, restaurant and pool."
Reviewed on Jun 24, 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.
Stay near popular Highland Square attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.