Highland Square Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Berrodin Bed & Breakfast

Berrodin Bed & Breakfast

3 out of 5
814 Bloomfield Ave Akron OH
0.61 km from Highland Square
Stay at this B&B in Akron. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Highland Theater and Dr. Bob's Home are located nearby.
Courtyard by Marriott Canton

Courtyard by Marriott Canton

3 out of 5
4375 Metro Cir Nw Canton OH
28.02 km from Highland Square
Book a stay at this business-friendly hotel in Canton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Kent State University Hotel and Conference Center

Kent State University Hotel and Conference Center

3.5 out of 5
215 S. Depeyster Street Kent OH
17.08 km from Highland Square
Book a stay at this business-friendly hotel in Kent. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Cleveland Macedonia

La Quinta Inn & Suites by Wyndham Cleveland Macedonia

3 out of 5
268 East Highland Rd Macedonia OH
22.36 km from Highland Square
Book a stay at this business-friendly hotel in Macedonia. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites Cuyahoga Falls - Akron

Comfort Inn & Suites Cuyahoga Falls - Akron

3 out of 5
1420 Main St Cuyahoga Falls OH
5.98 km from Highland Square
Book a stay at this business-friendly hotel in Cuyahoga Falls. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Aurora Inn

The Aurora Inn

3 out of 5
30 Shawnee Trail Aurora OH
29.54 km from Highland Square
Book a stay at this business-friendly hotel in Aurora. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
Courtyard by Marriott Akron Stow

Courtyard by Marriott Akron Stow

3 out of 5
4047 Bridgewater Pkwy Stow OH
10.39 km from Highland Square
Book a stay at this business-friendly hotel in Stow. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff ...
The Royal Inn & Suites

The Royal Inn & Suites

2.5 out of 5
2677 Gilchrist Rd Akron OH
10.56 km from Highland Square
Book a stay at this business-friendly hotel in Akron. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Best Western Plus North Canton Inn & Suites

Best Western Plus North Canton Inn & Suites

2.5 out of 5
6889 Sunset Strip Avenue NW North Canton OH
26.08 km from Highland Square
Book a stay at this business-friendly hotel in North Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Canton

Hyatt Place Canton

3 out of 5
5421 Whipple Ave NW North Canton OH
28.56 km from Highland Square
Book a stay at this business-friendly hotel in North Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Inn & Suites Akron South

Comfort Inn & Suites Akron South

2.5 out of 5
1025 Interstate Pkwy Akron OH
14.31 km from Highland Square
Book a stay at this business-friendly hotel in Akron. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Embassy Suites by Hilton Akron Canton Airport

Embassy Suites by Hilton Akron Canton Airport

3.5 out of 5
7883 Freedom Avenue, N.W. North Canton OH
24.76 km from Highland Square
Book a stay at this business-friendly hotel in North Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Cambria Hotel Akron - Canton Airport

Cambria Hotel Akron - Canton Airport

3 out of 5
1787 Thorn Drive Uniontown OH
16.91 km from Highland Square
Book a stay at this business-friendly hotel in Uniontown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Comfort Inn Hall of Fame

Comfort Inn Hall of Fame

2.5 out of 5
5345 Broadmoor Cir Nw Canton OH
29 km from Highland Square
Book a stay at this business-friendly hotel in Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Spark by Hilton Akron Fairlawn

Spark by Hilton Akron Fairlawn

3 out of 5
4073 Medina Road Akron OH
9.27 km from Highland Square
Book a stay at this business-friendly hotel in Akron. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. ...
Don't see what you're looking for?
See all available properties in Highland Square
View all properties
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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Aug 6 - Wed, Aug 19
FLL
Fort Lauderdale - Hollywood Intl.
CLE
Hopkins Intl.
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Fort Lauderdale - Hollywood Intl. to Hopkins Intl., returning Wed, Aug 19, priced at $105 found 4 days ago
Delta
Fri, Aug 14 - Mon, Aug 17
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$129 Roundtrip, found 6 days ago
$129
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Aug 14 from Hartsfield-Jackson Atlanta Intl. to Hopkins Intl., returning Mon, Aug 17, priced at $129 found 6 days ago
Breeze Airways
Wed, Sep 16 - Thu, Sep 24
MCO
Orlando Intl.
CAK
Akron-Canton
$132 Roundtrip, found 4 days ago
$132
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 16 from Orlando Intl. to Akron-Canton, returning Thu, Sep 24, priced at $132 found 4 days ago
American Airlines
Thu, Sep 3 - Sat, Sep 19
BOS
Logan Intl.
CAK
Akron-Canton
$310 Roundtrip, found 1 day ago
$310
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 3 from Logan Intl. to Akron-Canton, returning Sat, Sep 19, priced at $310 found 1 day ago