Guildwood Vacations from $403

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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.
Mount Alverno Luxury Resorts

Mount Alverno Luxury Resorts

2.5 out of 5
Save 100% on your flight
Price was $704, price is now $403 per person
$403
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
9/10 Wonderful! (314 reviews)
Room was nice overall, but bathroom supplies were lacking (not enough towels for 2 people, no extra toilet paper) and the sink did not drain properly. Breakfast and fruit/sweet tray were okay, but not what I would expect from a ‘luxury resort’. The staff were very friendly and did their best to be helpful.

Reviewed on Nov 14, 2025

GLOBALSTAY. Modern North York Condos

GLOBALSTAY. Modern North York Condos

4 out of 5
North York
Save 100% on your flight
Price was $818, price is now $528 per person
$528
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
6.6/10 (158 reviews)
Amazing stay, responsive host

Reviewed on Nov 16, 2025

Spacious 4-Bedroom Retreat

Spacious 4-Bedroom Retreat

3 out of 5
Save 100% on your flight
Price was $1,538, price is now $1,000 per person
$1,000
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
No reviews
Modern Lillian Street Condos Midtown Toronto

Modern Lillian Street Condos Midtown Toronto

4.5 out of 5
Old Toronto
Save 100% on your flight
Price was $665, price is now $440 per person
$440
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
7.2/10 Good! (123 reviews)
Amazing stay, responsive host

Reviewed on Nov 16, 2025

GLOBALSTAY. Charming Yorkville Condos

GLOBALSTAY. Charming Yorkville Condos

4 out of 5
Old Toronto
Save 100% on your flight
Price was $708, price is now $493 per person
$493
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
7.8/10 Good! (136 reviews)
Amazing stay, responsive host

Reviewed on Nov 16, 2025

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
$122 nightly
The price is $150 total per night from Dec 18 to Dec 19
$150 total
Dec 18 - Dec 19
Total with taxes and fees
8.2/10 Very Good! (13,115 reviews)
clean room, tv great . great ammenities

Reviewed on Nov 17, 2025

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
$122 nightly
The price is $149 total per night from Dec 15 to Dec 16
$149 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (4,821 reviews)
Room was very clean, staff were very friendly, location is excellent for taking the subway! Only issue we had was that our curtain in our room did not open

Reviewed on Nov 14, 2025

Holiday Inn Toronto Downtown Centre by IHG
Fairmont Royal York

Fairmont Royal York

4 out of 5
100 Front St West Toronto ON
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $252 total per night from Dec 16 to Dec 17
$252 total
Dec 16 - Dec 17
Total with taxes and fees
9/10 Wonderful! (7,401 reviews)
Great hotel, location, amenities and great bars.

Reviewed on Nov 13, 2025

Fairmont Royal York
See all 4,386 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

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
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 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

$33
per adult
90% 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)

$135
per adult
84% 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.