Highland Square Vacation Packages for 2026

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Highland Square Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Streetsboro, OH

Motel 6 Streetsboro, OH

2 out of 5
Price was $528, price is now $488 per person
$488
per person
Aug 21 - Aug 25
found 9 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Akron (CAK)
Book a stay at this business-friendly motel in Streetsboro. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions ZipCity and Boulder Creek Golf Club are located nearby.

Copley Inn & Suites By OYO Akron OH

Copley Inn & Suites By OYO Akron OH

2.5 out of 5
Price was $647, price is now $557 per person
$557
per person
Aug 21 - Aug 25
found 7 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Akron (CAK)
Book a stay at this business-friendly hotel in Akron. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Blossom Music Center and Summit Mall are located nearby.

Courtyard by Marriott Canton

Courtyard by Marriott Canton

3 out of 5
Price was $631, price is now $558 per person
$558
per person
Aug 21 - Aug 25
found 9 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Akron (CAK)
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. Popular attractions Pro Football Hall of Fame and Belden Village Mall are located nearby.

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

3 out of 5
Price was $741, price is now $702 per person
$702
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Akron (CAK)
Book a stay at this business-friendly hotel in Streetsboro. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions ZipCity and Hudson Springs Park are located nearby.

Fairfield Inn & Suites Akron Fairlawn

Fairfield Inn & Suites Akron Fairlawn

3 out of 5
Price was $705, price is now $669 per person
$669
per person
Aug 21 - Aug 25
found 7 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Akron (CAK)
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 in our reviews. Popular attractions Blossom Music Center and Summit Mall are located nearby.

Holiday Inn Express Hotel & Suites Cleveland-Streetsboro by IHG

Holiday Inn Express Hotel & Suites Cleveland-Streetsboro by IHG

2.5 out of 5
Price was $703, price is now $668 per person
$668
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Akron (CAK)
Book a stay at this business-friendly hotel in Streetsboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ZipCity and Boulder Creek Golf Club are located nearby.

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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. ...
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 ...
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 ...
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 ...
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 WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 ...
Hawthorn Extended Stay by Wyndham Seville

Hawthorn Extended Stay by Wyndham Seville

3 out of 5
5025 Park Ave W Seville OH
27.95 km from Highland Square
Book a stay at this business-friendly hotel in Seville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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 ...
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 ...
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. ...
Baymont by Wyndham Copley Akron

Baymont by Wyndham Copley Akron

2.5 out of 5
130 Montrose West Ave Akron OH
9.56 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 ...
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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
Tue, Aug 4 - Mon, Aug 17
MCO
Orlando Intl.
CLE
Hopkins Intl.
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Orlando Intl. to Hopkins Intl., returning Mon, Aug 17, priced at $98 found 6 days ago
Delta
Tue, Jul 28 - Sat, Aug 1
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$119 Roundtrip, found 6 hours ago
$119
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Jul 28 from Hartsfield-Jackson Atlanta Intl. to Hopkins Intl., returning Sat, Aug 1, priced at $119 found 6 hours ago
Breeze Airways
Sun, Aug 30 - Sun, Sep 6
TPA
Tampa Intl.
CAK
Akron-Canton
$164 Roundtrip, found 20 hours ago
$164
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Sun, Aug 30 from Tampa Intl. to Akron-Canton, returning Sun, Sep 6, priced at $164 found 20 hours ago
United
Thu, Aug 13 - Sat, Aug 22
BOS
Logan Intl.
CLE
Hopkins Intl.
$169 Roundtrip, found 10 hours ago
$169
Roundtrip
found 10 hours ago
Select United flight, departing Thu, Aug 13 from Logan Intl. to Hopkins Intl., returning Sat, Aug 22, priced at $169 found 10 hours ago
American Airlines
Tue, Jul 21 - Mon, Aug 3
JFK
John F. Kennedy Intl.
CLE
Hopkins Intl.
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 21 from John F. Kennedy Intl. to Hopkins Intl., returning Mon, Aug 3, priced at $187 found 1 day ago