Playhouse Square Vacation Packages 2025/2026 from $280

Playhouse Square flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Willoughby House

$280

per person

Nov 14 - Nov 16

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Cleveland (CLE)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.

Berlin Heritage Inn

$355

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Cleveland (CLE)

This motel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A terrace, luggage storage, and concierge services are also on offer.

Sprucewood Inn

$285

per person

Oct 17 - Oct 21

found 4 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Cleveland (CLE)

An outdoor pool is featured at this motel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden and a picnic area are also provided.

The Hotel At Oberlin

$672

per person

Oct 17 - Oct 21

found 3 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Cleveland (CLE)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Sycamore Suites

$342

per person

Oct 17 - Oct 21

found 5 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Cleveland (CLE)

This hotel features an outdoor pool and an indoor pool. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Top Playhouse Square hotels deals

Ramada by Wyndham Cleveland Independence

5300 Rockside Road, Independence, OH

Free Cancellation

Reserve now, pay when you stay

$57 nightly

$67 total

Sep 8 - Sep 9

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and a garden are also provided.

Pool

Breakfast included

The Westin Cleveland Downtown

777 Saint Clair Ave Ne, Cleveland, OH

$129 nightly

$152 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, dry cleaning, and free newspapers are also on offer.

Pet friendly

Free WiFi

La Quinta Inn & Suites by Wyndham Cleveland - Airport North

4222 W 150th St, Cleveland, OH

Free Cancellation

Reserve now, pay when you stay

$91 nightly

$107 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a gym on site, and a 24-hour front desk and a convenience store are also provided.

Breakfast included

Free airport shuttle

Hotel Indigo Cleveland Downtown by IHG

651 Huron Rd E, Cleveland, OH

Free Cancellation

$95 nightly

$112 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, express check-in, and express check-out are also on offer.

Pet friendly

Free WiFi

Hyatt Regency Cleveland At The Arcade

420 Superior Ave E, Cleveland, OH

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$154 total

Sep 29 - Sep 30

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a lobby fireplace, and a hair salon are also on offer.

Spa

Pet friendly

Hilton Cleveland Downtown

100 Lakeside Ave East, Cleveland, OH

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$199 total

Oct 5 - Oct 6

Total with taxes and fees

The hotel's indoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 17 conference rooms on site, along with the valet parking and WiFi in public areas. A restaurant, a 24-hour front desk, and a coffee shop are also provided.

Pool

Pet friendly

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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.

Popular places to visit

Rock and Roll Hall of Fame

4.5/5(1,043 reviews)

Discover the music and memorabilia from the greatest rock bands in the world and find out why Cleveland is so important to the world of Rock and Roll.

Huntington Bank Field

4.5/5(294 reviews)

Catch an event at Huntington Bank Field during your trip to Cleveland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Beautiful ballpark, right in the heart of downtown Cleveland.

Cleveland Indians - 7
Minnesota Twins - 6

Progressive Field

4.5/5(473 reviews)

Catch an event at Progressive Field during your trip to Cleveland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Frequently asked questions

How much are vacation packages to Playhouse Square?

Starting from as little as $280, hotel and flight packages are a fabulous way to make your budget stretch further. Playhouse Square, here you come!

Where can I get the best vacation package deals for Playhouse Square?

You can lock in unbeatable Playhouse Square package deals with Travelocity. Pick from 400 airlines and 1,000,000 properties worldwide and turn those vacation daydreams into a reality.

Why should I book my Playhouse Square vacation bundle via Travelocity?

With our Price Match Guarantee, we'll match any cheaper price you find. Add to that our 24/7 customer support and top-quality service and the vacation of your dreams is well within reach.

Can I save on my Playhouse Square car rental if I bundle it with my hotel or flight?

Certainly — and if you also add a tour or an experience to your Playhouse Square vacation package, you'll pick up even greater savings. With a package, you can find things to do around the region that are right up your alley. Then, jump in your rental car and work your way through the list. Geneva State Park is one fantastic sight to put on your itinerary. It's located 45 mi from Playhouse Square.