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.
Country Inn & Suites by Radisson, Macedonia, OH

Country Inn & Suites by Radisson, Macedonia, OH

3 out of 5
Price was $353, price is now $310 per person
$310
per person
Feb 5 - Feb 9
found 12 hours ago
Roundtrip non-stop flight included
New York (LGA) to Akron (CAK)
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 staff in our reviews. Popular attractions Cuyahoga Valley National Park and MGM Northfield Park 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.
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 ...
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 ...
Econo Lodge Cleveland Southeast - Kent

Econo Lodge Cleveland Southeast - Kent

2 out of 5
9789 State Route 14 Streetsboro OH
22.77 km from Highland Square
Stay at this hotel 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. ...
Radisson Hotel Akron/Fairlawn

Radisson Hotel Akron/Fairlawn

3 out of 5
200 Montrose West Ave Akron OH
9.51 km from Highland Square
Book a stay at this business-friendly hotel in Akron. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Rosemont Country Club and ...
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 ...
Hampton Inn & Suites Oakwood Village-Cleveland

Hampton Inn & Suites Oakwood Village-Cleveland

2.5 out of 5
23300 Oakwood Commons Drive Oakwood Village OH
30.05 km from Highland Square
Book a stay at this business-friendly hotel in Oakwood Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hilton Garden Inn Akron Canton Airport

Hilton Garden Inn Akron Canton Airport

3 out of 5
5251 Landmark Blvd North Canton OH
23.19 km from Highland Square
Book a stay at this business-friendly hotel in North Canton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hampton Inn Akron-South

Hampton Inn Akron-South

2.5 out of 5
880 Arlington Ridge East Akron OH
13.59 km from Highland Square
Stay at this hotel in Akron. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
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 ...
Fairfield Inn & Suites Akron Fairlawn

Fairfield Inn & Suites Akron Fairlawn

2.5 out of 5
208 Springside Dr Akron OH
9.39 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 ...
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 ...
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 ...
Extended Stay America Suites Akron Copley East

Extended Stay America Suites Akron Copley East

2.5 out of 5
185 Montrose West Ave Akron OH
9.49 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 in our reviews. ...
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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
Fri, Jan 16 - Sun, Jan 18
BOS
Logan Intl.
CLE
Hopkins Intl.
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Jan 16 from Logan Intl. to Hopkins Intl., returning Sun, Jan 18, priced at $68 found 6 days ago
Spirit Airlines
Wed, Jan 7 - Thu, Jan 8
FLL
Fort Lauderdale - Hollywood Intl.
CLE
Hopkins Intl.
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jan 7 from Fort Lauderdale - Hollywood Intl. to Hopkins Intl., returning Thu, Jan 8, priced at $90 found 2 days ago
Delta
Tue, Jan 13 - Wed, Jan 21
BOS
Logan Intl.
CLE
Hopkins Intl.
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jan 13 from Logan Intl. to Hopkins Intl., returning Wed, Jan 21, priced at $157 found 6 days ago
JetBlue Airways
Tue, Jan 13 - Thu, Jan 22
BOS
Logan Intl.
CLE
Hopkins Intl.
$162 Roundtrip, found 6 days ago
$162
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Jan 13 from Logan Intl. to Hopkins Intl., returning Thu, Jan 22, priced at $162 found 6 days ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 9 from Hartsfield-Jackson Atlanta Intl. to Hopkins Intl., returning Sun, Jan 11, priced at $239 found 1 day ago