Guildwood Vacations from $734

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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.

Modern Apartments in North York

North York

$734

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip flight included

New York (NYC) to Toronto (YYZ)

8.2/10 Very Good! (373 reviews)

Room was not as expected or as the pictures showed. I think there are many units offered there and I happened to get one of the older ones. The communication was swift only in relation to connecting payment and when I brought up my concerns I never got an answer.

Reviewed on Aug 26, 2026

1 Hotel Toronto

Downtown Toronto

$2,314

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (789 reviews)

Hotel Riu Plaza Toronto

Downtown Toronto

$1,321

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.4/10 Exceptional! (4,590 reviews)

For a hotel in the heart of downtown, it was a solid stay. Very close to many tourist attractions, restaurants, popular streets, and minutes away from the TTC. The hotel breakfast was very worth it. The hotel staff was very kind — we were granted an early check-in at no extra charge. Only minor notes were that the room we booked was quite small for four people. The sliding washroom door in our room was also translucent to the point where it was a little awkward to use because we could see each other’s silhouette. Aside from that, the hotel itself was very clean, provided great amenities, and was a great place to sleep and recharge while we spent most of our visit exploring the city.

Reviewed on Aug 29, 2026

Modern Lillian Street Condos Midtown Toronto

Old Toronto

$812

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip flight included

New York (NYC) to Toronto (YYZ)

8.4/10 Very Good! (313 reviews)

Terrible.

Reviewed on Aug 17, 2026

Shangri-La Toronto

Downtown Toronto

$2,160

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (1,350 reviews)

Where to stay in Guildwood

Find the best Guildwood areas and neighborhoods for the activities you enjoy most. Learn more about Guildwood

A row of international flags in front of a historic building with ornate architecture.

Downtown Toronto

6 out of top 10 points of interest in this area

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.

A well-manicured garden with geometric hedges, a variety of flowering plants, and a central tall tree.

North York

1 out of top 10 points of interest in this area

Home to interactive museums like Ontario Science Centre and Aga Khan Museum, North York offers ample shopping at Yorkdale Shopping Centre and Fairview Mall. Easily accessible via TTC subway and bus lines.

A row of Victorian-style houses with steep gabled roofs, surrounded by lush greenery and a well-maintained lawn.

Etobicoke

Suburban and industrialized, Etobicoke boasts numerous parks like James Gardens and Centennial Park, as well as golf courses such as St. George's Golf and Country Club. Enjoy convenient public transportation via TTC and GO stations.

A large wooden climbing structure with multiple levels and ropes.

Scarborough

1 out of top 10 points of interest in this area

Situated atop Scarborough Bluffs, this diverse district offers shopping at Scarborough Town Centre and animal encounters at Toronto Zoo. Explore natural landmarks like Rouge Park and the Scarborough Bluffs, or hop on the TTC for easy transit access.

An aerial view of a city with a river, high-rise buildings, and a bridge.

Toronto Entertainment District

Downtown Toronto's vibrant hub features theatres, performing arts centres, and Toronto Blue Jays games, with numerous bars and restaurants catering to diverse crowds. Don't miss the iconic CN Tower!

Guildwood Hotel Deals

Chelsea Hotel, Toronto

33 Gerrard St W Toronto ON

Fully refundableReserve now, pay when you stay

$152 nightly

$182 total

Sep 7 - Sep 8

Total with taxes and fees

Toronto Don Valley Hotel and Suites

175 Wynford Drive Toronto ON

$107 nightly

$128 total

Aug 30 - Aug 31

Total with taxes and fees

Fairmont Royal York

100 Front St West Toronto ON

Fully refundableReserve now, pay when you stay

$232 nightly

$278 total

Sep 3 - Sep 4

Total with taxes and fees

See all 5,845 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.