Highland Square Vacation Packages for 2025

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

Photo by Melodie Hayes
Choose two or more items and save on your trip:

Highland Square Flight + Hotel packages

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

Motel 6 Richfield, OH

2 out of 5
per person
Oct 2 - Oct 7
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Akron (CAK)
Stay at this motel in Richfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. Popular attractions Cuyahoga Valley National Park and Furnace Run Metro Park are located nearby.

La Quinta Inn & Suites by Wyndham Cleveland Macedonia

La Quinta Inn & Suites by Wyndham Cleveland Macedonia

3 out of 5
per person
Oct 2 - Oct 7
found 11 hours ago
Roundtrip flight included
Denver (DEN) 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.

Don't see what you're looking for?
See all available trips from Columbus to Highland Square
View all trips

Top Hotel Deals

Radisson Hotel Akron/Fairlawn

Radisson Hotel Akron/Fairlawn

3 out of 5
200 Montrose West Ave, Akron, OH
10 km from Highland Square
Stay at this 3-star business-friendly hotel in Akron. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Rosemont Country Club and ...
Econo Lodge Cleveland Southeast - Kent

Econo Lodge Cleveland Southeast - Kent

2 out of 5
9789 State Route 14, Streetsboro, OH
22.71 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. ...
Hyatt Place Canton

Hyatt Place Canton

3 out of 5
5421 Whipple Ave NW, North Canton, OH
28.15 km from Highland Square
Stay at this 3-star 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
22.6 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 ...
Quality Inn

Quality Inn

2.5 out of 5
2873 S Arlington Rd, Akron, OH
12.29 km from Highland Square
Stay at this hotel in Akron. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Firestone ...
Wingate by Wyndham Canton/Hall of Fame

Wingate by Wyndham Canton/Hall of Fame

2.5 out of 5
4914 Everhard Road NW, Canton, OH
28.59 km from Highland Square
Stay at this hotel in Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Belden ...
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
16.8 km from Highland Square
Stay at this 3.5-star business-friendly hotel in Kent. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Country Inn & Suites by Radisson, Canton near Hall of Fame

Country Inn & Suites by Radisson, Canton near Hall of Fame

2.5 out of 5
5335 Broadmoor Circle Nw, Canton, OH
28.54 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 helpful staff and the clean rooms ...
Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
4742 Brecksville Rd, Richfield, OH
19.93 km from Highland Square
Book a stay at this family-friendly hotel in Richfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Comfort Inn & Suites Cuyahoga Falls - Akron

Comfort Inn & Suites Cuyahoga Falls - Akron

3 out of 5
1420 Main St, Cuyahoga Falls, OH
5.75 km from Highland Square
Stay at this 3-star business-friendly hotel in Cuyahoga Falls. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn Hall of Fame

Comfort Inn Hall of Fame

2.5 out of 5
5345 Broadmoor Cir Nw, Canton, OH
28.58 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 ...
Super 8 by Wyndham Copley Akron

Super 8 by Wyndham Copley Akron

2.5 out of 5
130 Montrose West Ave, Building B, Akron, OH
10.05 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 ...
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
24.33 km from Highland Square
Stay at this 3.5-star business-friendly hotel in North Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites Copley Akron

Comfort Inn & Suites Copley Akron

2.5 out of 5
160 Montrose West Ave, Akron, OH
10.01 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 ...
DoubleTree by Hilton Akron Fairlawn

DoubleTree by Hilton Akron Fairlawn

3 out of 5
3180 W Market St, Akron, OH
7.19 km from Highland Square
Stay at this 3-star business-friendly hotel in Akron. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property ...
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
Sat, Aug 2 - Thu, Aug 7
MCO
Orlando Intl.
CLE
Hopkins Intl.
$82 Roundtrip, found 4 days ago
$82
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 2 from Orlando Intl. to Hopkins Intl., returning Thu, Aug 7, priced at $82 found 4 days ago
Breeze Airways
Thu, Aug 21 - Tue, Aug 26
MCO
Orlando Intl.
CAK
Akron-Canton
$107 Roundtrip, found 10 hours ago
$107
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Thu, Aug 21 from Orlando Intl. to Akron-Canton, returning Tue, Aug 26, priced at $107 found 10 hours ago
Spirit Airlines
Sat, Sep 27 - Sun, Sep 28
FLL
Fort Lauderdale - Hollywood Intl.
CLE
Hopkins Intl.
$117 Roundtrip, found 17 hours ago
$117
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Sat, Sep 27 from Fort Lauderdale - Hollywood Intl. to Hopkins Intl., returning Sun, Sep 28, priced at $117 found 17 hours ago
United
Fri, Sep 12 - Mon, Sep 15
EWR
Newark Liberty Intl. Airport
CLE
Hopkins Intl.
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Select United flight, departing Fri, Sep 12 from Newark Liberty Intl. Airport to Hopkins Intl., returning Mon, Sep 15, priced at $189 found 5 days ago
American Airlines
Fri, Aug 8 - Wed, Aug 13
LGA
LaGuardia
CLE
Hopkins Intl.
$194 Roundtrip, found 6 days ago
$194
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Aug 8 from LaGuardia to Hopkins Intl., returning Wed, Aug 13, priced at $194 found 6 days ago