Playhouse Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Playhouse Square

Price found within the past 48 hours. Click for updated prices.
The Tudor Arms Hotel Cleveland - a DoubleTree by Hilton

The Tudor Arms Hotel Cleveland - a DoubleTree by Hilton

4 out of 5
University Circle
per person
Jun. 23 - Jun. 27
found 8 hours ago
Roundtrip flight included
Saskatoon (YXE) to Cleveland (CLE)
8.2/10 Very Good! (1,010 reviews)
The architecture was amazing, friendly staff, on site restaurant was very convenient but a little pricey, and the shuttle driver knew his way around Cleveland clinic which took a lot of stress off of us. Would definitely stay there again.

Reviewed on Apr. 17, 2025

Fidelity Hotel

Fidelity Hotel

4 out of 5
Downtown Cleveland
per person
Jun. 8 - Jun. 12
found 8 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Cleveland (CLE)
9.8/10 Exceptional! (31 reviews)
Valet alittle confusing and had to wait a while for the car when we left, otherwise everything else was great

Reviewed on Apr. 18, 2025

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

4 out of 5
Downtown Cleveland
per person
Jun. 23 - Jun. 27
found 8 hours ago
Roundtrip flight included
Saskatoon (YXE) to Cleveland (CLE)
7.2/10 Good! (1,126 reviews)
Very clean and staff was awesome!

Reviewed on Apr. 11, 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
per person
Jun. 8 - Jun. 12
found 8 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Cleveland (CLE)
8.6/10 Excellent! (1,203 reviews)
Excellent property ,, clean very well located,, excellent staff,, great service at valet parking

Reviewed on Apr. 18, 2025

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
per person
Jun. 23 - Jun. 27
found 8 hours ago
Roundtrip flight included
Saskatoon (YXE) to Cleveland (CLE)
7.4/10 Good! (1,001 reviews)
The staff were wonderful, the room clean, the breakfast was fantastic! Parking was easy and I will stay here again!

Reviewed on Apr. 10, 2025

Where to stay in Playhouse Square

Find the best Playhouse Square areas and neighborhoods for the activities you enjoy most. Learn more about Playhouse Square
Terminal Tower which includes railway items and heritage architecture

Downtown Cleveland

5 out of top 10 points of interest in this area

Diverse architecture and subdistricts define this central business area, offering various dining, retail, and entertainment options. Explore Playhouse Square, Public Square, and North Coast Harbor's attractions, with convenient access via the HealthLine and Waterfront Line Rapid stations.

Find hotels in Downtown Cleveland

Playhouse Square Hotel Deals

The Westin Cleveland Downtown
The Westin Cleveland Downtown
4 out of 5
777 Saint Clair Ave Ne, Cleveland, OH
The price is CA $151 per night from Apr. 24 to Apr. 25
CA $151
CA $177 total
includes taxes & fees
Apr 24 - Apr 25
8.4/10 Very Good! (1,248 reviews)
"Very Nice"

Reviewed on Apr. 16, 2025

The Westin Cleveland Downtown
Hotel Indigo Cleveland Downtown by IHG
Hotel Indigo Cleveland Downtown by IHG
3.5 out of 5
651 Huron Rd E, Cleveland, OH
Fully refundable
The price is CA $143 per night from Apr. 24 to Apr. 25
CA $143
CA $168 total
includes taxes & fees
Apr 24 - Apr 25
8.4/10 Very Good! (1,115 reviews)
"Good hotel overall. The bathroom was very small in the room I stayed."

Reviewed on Apr. 17, 2025

Hotel Indigo Cleveland Downtown by IHG
Drury Plaza Hotel Cleveland Downtown
Drury Plaza Hotel Cleveland Downtown
3 out of 5
1380 East 6th Street, Cleveland, OH
The price is CA $166 per night from May 6 to May 7
CA $166
CA $195 total
includes taxes & fees
May 6 - May 7
9.4/10 Exceptional! (2,437 reviews)
"Loved our stay at the Drury Hotel in Cleveland! Conveniently located to numerous locations and staff was outstanding!"

Reviewed on Apr. 17, 2025

Drury Plaza Hotel Cleveland Downtown
See all 1,620 properties in Playhouse Square
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Playhouse Square vacation package cost?
We make it easy to travel the world, with Playhouse Square packages starting from as low as CA $1,094. You’ll have the flexibility to bundle your favorite airlines, hotels and car rental. For the ultimate getaway, why not add some tours and activities to your itinerary?
How do I get a cheap travel package to Playhouse Square?
Browse and lock in everything all in one place with our Playhouse Square vacation packages. We have incredible bargains on flights, hotels and more that’ll keep your wallet happy and your sense of adventure alive. And, with more than 550 partner airlines and 1,000,000 hotels throughout the world to select from, you have countless opportunities to mix and match as you like.
Where should I stay in Playhouse Square?
A visit to Playhouse Square isn’t over until you’ve seen Progressive Field and Rock and Roll Hall of Fame. Book a hotel nearby for quick access to these fantastic sights.
What are the top hotels in Playhouse Square?
When it comes to comfortable and convenient places to stay in Playhouse Square, you can’t go past Crowne Plaza Cleveland at Playhouse Square, an IHG Hotel. Check out our deals and land a great price.
How far in advance should I book my Playhouse Square vacation?
It can be hard to know when is the ideal time to book your Playhouse Square vacation. But generally the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels nearly a year before departure. If you’re considering a last-minute getaway, no need to worry! There are plenty of fantastic deals posted on Expedia all the time.
What does an Expedia Playhouse Square travel package include?
Choose from any combination of flights, rental cars and hotels. Once you’ve made your booking, you can also add on tours and activities. Want to pick your fare class? That’s also possible. The choice is yours when it comes to crafting your perfect Playhouse Square getaway.
What should I know before booking a Playhouse Square travel package?
Our prices are always low. However, you’ll enjoy even better deals when you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and tons of choice.
Can I choose my airline with a Playhouse Square Expedia vacation package?
Most definitely. We offer more than 550 airlines worldwide, so you can design your Playhouse Square adventure according to your travel needs.
If I'm not able to travel, can I cancel my Playhouse Square vacation package?
We totally understand that life can throw you the odd curveball. If you’ve locked in a Playhouse Square vacation package and need to cancel or change it, we’re here to help. We suggest taking a look at our Customer Service Portal first for information. But generally, if you’ve booked your package in the last 24 hours, you may be able to cancel and rebook free of charge. If it’s been more than 24 hours, your airline, hotel or car rental company may impose a fee.

Discover the most popular places to visit in Playhouse Square

Progressive Field

Progressive Field

4.5/5(44 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.

Progressive Field
Rock and Roll Hall of Fame featuring interior views and music

Rock and Roll Hall of Fame

4.5/5(117 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.

Rock and Roll Hall of Fame
Huntington Bank Field

Huntington Bank Field

4.5/5(38 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.

Huntington Bank Field

Things to do

Cleveland: Eerie Ghosts Haunted Walking Tour

Cleveland: Eerie Ghosts Haunted Walking Tour

CA $46
per adult
Cleveland: Eerie Ghosts Haunted Walking Tour
Hear Haunted Histories on Our cleveland Ghost Tour.

Cleveland Ghosts Tour

CA $37
per adult
100% of travellers recommend
Cleveland Ghosts Tour
The Escape Game: Epic 60-Minute Adventures at Crocker Park

The Escape Game: Epic 60-Minute Adventures at Crocker Park

CA $57
per adult
The Escape Game: Epic 60-Minute Adventures at Crocker Park
See all activities in Cleveland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.