Playhouse Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Playhouse Square

Price found within the past 48 hours. Click for updated prices.
Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was CA $1,537, price is now CA $1,322 per person
CA $1,322
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Cleveland (CLE)
9/10 Wonderful! (1,062 reviews)
Excellent stay

Reviewed on Nov 9, 2026

ROOST Cleveland

ROOST Cleveland

4 out of 5
Downtown Cleveland
Price was CA $1,681, price is now CA $1,461 per person
CA $1,461
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Cleveland (CLE)
9.6/10 Exceptional! (848 reviews)
5 stars, will be returning next time I take a trip to the Land.

Reviewed on Nov 9, 2026

Wyndham Avon

Wyndham Avon

3.5 out of 5
Price was CA $1,551, price is now CA $1,382 per person
CA $1,382
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Cleveland (CLE)
8.8/10 Excellent! (1,091 reviews)
clean, staff was friendly. bed was comfortable. Would definitely stay there again.

Reviewed on Nov 7, 2026

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Price was CA $1,501, price is now CA $1,351 per person
CA $1,351
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Cleveland (CLE)
8.8/10 Excellent! (372 reviews)
The main lobby was freezing. It seemed like they had the air conditioning running. Stay was great, food was great, and would stay again.

Reviewed on Nov 8, 2026

Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

4 out of 5
Downtown Cleveland
Price was CA $1,623, price is now CA $1,465 per person
CA $1,465
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Cleveland (CLE)
9/10 Wonderful! (1,330 reviews)

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
A grand building facade with large arched windows and ornate columns.

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

Extended Stay America Premier Suites - Cleveland - Independence

Extended Stay America Premier Suites - Cleveland - Independence

2.5 out of 5
6025 Jefferson Dr Independence OH
Fully refundableReserve now, pay when you stay
The price is CA $72 per night from Dec 10 to Dec 11
CA $72
CA $85 total
Dec 10 - Dec 11
includes taxes & fees
7/10 Good! (1,877 reviews)
"Toilet ran continuously. A/C UNIT was short cycling and nosie.over all the place is got alot of miles on it.Would not stay here again."

Reviewed on Nov 8, 2026

Extended Stay America Premier Suites - Cleveland - Independence
The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
777 Saint Clair Ave Ne Cleveland OH
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Nov 22 to Nov 23
CA $182
CA $214 total
Nov 22 - Nov 23
includes taxes & fees
8.8/10 Excellent! (422 reviews)
"The main lobby was freezing. It seemed like they had the air conditioning running. Stay was great, food was great, and would stay again."

Reviewed on Nov 8, 2026

The Westin Cleveland Downtown
Best Western Plus Strongsville Cleveland

Best Western Plus Strongsville Cleveland

3 out of 5
15471 Royalton Rd Strongsville OH
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Nov 10 to Nov 11
CA $94
CA $111 total
Nov 10 - Nov 11
includes taxes & fees
7.8/10 Good! (1,748 reviews)
"The breakfast was the worst. No toaster, no hot food, nothing decent to eat. Thank goodness I bring my personal coffee maker. Did not even bother to check the 2nd morning. No ice machine in several floors, only one operating elevator and the building was huge. Ran out of toilet paper, called the ..."

Reviewed on Nov 9, 2026

Best Western Plus Strongsville Cleveland
See all 1,827 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.
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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 $1,322. 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.

Stay near popular Playhouse Square attractions

Cleveland Play House

9.8/10 (6 reviews)
You can make plans for a show at Cleveland Play House during your stay in Cleveland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

Things to do

Cleveland: Eerie Ghosts Haunted Walking Tour

Phantom's Parade on Prospect: Cleveland Ghost Tours

CA $45
per adult
100% of travellers recommend
Phantom's Parade on Prospect: Cleveland Ghost Tours
Phantom's Parade on Prospect: Cleveland Ghost Tours

Phantom's Parade on Prospect: Cleveland Ghost Tours

CA $37
per adult
90% of travellers recommend
Phantom's Parade on Prospect: Cleveland Ghost Tours
Picture 3 for Activity Cleveland: Museum of Illusions Entry Ticket

Museum of Illusions Cleveland Entry Ticket

CA $48
per adult
100% of travellers recommend
Museum of Illusions Cleveland Entry Ticket
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.