Guildwood Vacations from $587

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Your Guildwood Vacation

Experience everything this neighborhood has to offer with a customized Guildwood vacation package. However you imagine spending your days here, you'll find endless opportunities for fun, adventure and relaxation. Kick off your trip to Guildwood by checking out nearby attractions such as University of Toronto Scarborough, Centennial College and Guild Inn Gardens. Don't just wish for it — make it happen! Reserve your ideal Guildwood vacation with Expedia and travel your way.

The Latest Guildwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Toronto Downtown / Entertainment District

Residence Inn by Marriott Toronto Downtown / Entertainment District

3.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $896, price is now $587 per person
$587
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.2/10 Wonderful! (3,171 reviews)
Room was Great, more than an average hotel room

Reviewed on Jan 12, 2026

Spacious 4-Bedroom Retreat

Spacious 4-Bedroom Retreat

3 out of 5
Save 100% on your flight
Price was $1,819, price is now $1,028 per person
$1,028
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
No reviews
Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,019, price is now $597 per person
$597
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.2/10 Wonderful! (451 reviews)
It should be make clearly on your web page that there is no parking at the Hotel. Parking is at municipal parking lots near by. I paid $50 to park from 3pm on Friday , until noon on Saturday. My stay at the hotel was excellent, the breakfast was also excellent, staff was excellent.

Reviewed on Jan 13, 2026

151 Dan Leckie Way

151 Dan Leckie Way

2.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,030, price is now $646 per person
$646
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.2/10 Wonderful! (278 reviews)
Cozy Winter Getaway Near the CN Tower Visiting my family here during the cold winter season was truly delightful. I didn’t have to worry about cleaning bulky winter clothing, and shopping and dining were incredibly convenient. The area around the CN Tower is especially charming on snowy days—perfect for a peaceful walk and soaking in the winter atmosphere. The only minor downside was the occasional consistent noise from the nearby train depot, but it didn’t take away from the overall experience. Also, Host was very kind and professional to communicate.

Reviewed on Jan 7, 2026

Homewood Suites by Hilton Toronto Vaughan

Homewood Suites by Hilton Toronto Vaughan

3 out of 5
Price was $1,173, price is now $758 per person
$758
per person
Mar 15 - Mar 20
found 19 hours ago
Roundtrip flight included
New York (JFK) to Toronto (YYZ)
8.6/10 Excellent! (1,005 reviews)
Pool could have used a cleaning, but everything else was great

Reviewed on Jan 13, 2026

Where to stay in Guildwood

Find the best Guildwood areas and neighborhoods for the activities you enjoy most. Learn more about Guildwood
Downtown Toronto featuring a city, an administrative buidling and heritage architecture

Downtown Toronto

5 out of top 10 points of interest in this area
4.5/5(4,700 area reviews)

Dive into the bustling Entertainment District with its lively restaurants, nightclubs, and live theatre, or explore the upscale Yorkville area, boasting designer boutiques and world-class galleries. Don't miss the iconic Royal Ontario Museum and the revitalized Harbourfront area.

Find hotels in Downtown Toronto

Guildwood Hotel Deals

Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $169 total per night from Feb 13 to Feb 14
$169 total
Feb 13 - Feb 14
Total with taxes and fees
8.4/10 Very Good! (13,760 reviews)
Very clean and nice play to stay

Reviewed on Jan 12, 2026

Chelsea Hotel, Toronto
Holiday Inn Toronto Downtown Centre by IHG

Holiday Inn Toronto Downtown Centre by IHG

3.5 out of 5
30 Carlton Street Toronto ON
Fully refundable
$120 nightly
The price is $147 total per night from Feb 1 to Feb 2
$147 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (5,198 reviews)
Clean and reasonably priced

Reviewed on Jan 12, 2026

Holiday Inn Toronto Downtown Centre by IHG
Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
30 Widmer St Toronto ON
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $176 total per night from Jan 15 to Jan 16
$176 total
Jan 15 - Jan 16
Total with taxes and fees
9/10 Wonderful! (1,330 reviews)
Great

Reviewed on Jan 12, 2026

Hotel Riu Plaza Toronto
See all 4,670 properties in Guildwood
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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Guildwood

Rogers Centre which includes signage and a city

Rogers Centre

Come to this multipurpose stadium to watch baseball matches and football games, listen to concerts of famous bands, see family shows or simply tour this central entertainment complex.

Rogers Centre
CN Tower showing skyline, a city and modern architecture

CN Tower

Take the glass elevator to the lookout points on Toronto’s iconic landmark to enjoy views as far as Niagara Falls or have dinner in high style.

CN Tower
CN Tower which includes rides

Canada's Wonderland

The highlight at this amusement park is the super-fast Leviathan ride, but there are 15 other roller coasters and more than 200 attractions to explore.

Canada's Wonderland

Things to do

Toronto: Ripley's Aquarium of Canada Entry Ticket

Toronto: Ripley's Aquarium of Canada Entry Ticket

$34
per adult
94% of travellers recommend
Toronto: Ripley's Aquarium of Canada Entry Ticket
Niagara Falls lit up at night with firework show nearby

Niagara Falls Day & Night Tour - Cruise & Dinner (Optional)

$124
per adult
86% of travellers recommend
Niagara Falls Day & Night Tour - Cruise & Dinner (Optional)
The highlight of any visit to the Hockey Hall of Fame is the Esso Great Hall, where guests can get close up to hockey's greatest treasure, the Stanley Cup.

Hockey Hall of Fame Admission Ticket

$18
per adult
90% of travellers recommend
Hockey Hall of Fame Admission Ticket
See all activities in Toronto
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.