Willowdale Vacations from $502

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Your Willowdale Vacation

Shopping, cafes and dining are just a few of the things waiting for you when you lock in a vacation package to Willowdale. Whether you're searching for adventure or relaxation, this trendy neighborhood will have it. When it's time to head out and explore, you'll find plenty of awesome attractions nearby including Fairview Mall, Seneca College and Bayview Village Shopping Centre. Visit one, two or all during your trip to Willowdale. Expedia can put your plans into action. Book your dream Willowdale vacation now.

The Latest Willowdale Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sterling Inn & Spa - an Ontario's Finest Inn

Sterling Inn & Spa - an Ontario's Finest Inn

4 out of 5
Clifton Hill
Price was $691, price is now $502 per person
$502
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.6/10 Exceptional! (1,989 reviews)
Love how the room was very clean and decorated beautifully with rose pebbles.

Reviewed on Sep 15, 2025

Woodbourne Inn

Woodbourne Inn

4 out of 5
St. Davids
Save 100% on your flight
Price was $1,252, price is now $834 per person
$834
per person
Oct 25 - Oct 31
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.8/10 Exceptional! (495 reviews)
We, mother and daughter from Japan enjoyed every minute of our stay at Woodbourne Inn. Warm welcome, beautiful place, great breakfast, and so on. A winery with an excellent restaurant is within walking distance.

Reviewed on Aug 24, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,393, price is now $957 per person
$957
per person
Nov 20 - Nov 23
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (587 reviews)
Clean room, nice restaurants and polite staff.

Reviewed on Sep 8, 2025

GLOBALSTAY Modern Lillian St Apartments

GLOBALSTAY Modern Lillian St Apartments

4.5 out of 5
Old Toronto
Save 100% on your flight
Price was $1,108, price is now $803 per person
$803
per person
Oct 16 - Oct 21
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
7.2/10 Good! (109 reviews)
Property was great. Location very close to public transit. Check in process is a bit "unique" and a little confusing but it works. You get good value for your money.

Reviewed on Sep 7, 2025

The Pearl Waterfront Estate

The Pearl Waterfront Estate

4.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $4,187, price is now $3,085 per person
$3,085
per person
Nov 22 - Nov 25
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
4/10 (4 reviews)

Where to stay in Willowdale

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

Willowdale Hotel Deals

Novotel Toronto North York

Novotel Toronto North York

3.5 out of 5
3 Park Home Avenue, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is $190 total per night from Oct 12 to Oct 13
$190 total
per night
Oct 12 - Oct 13
8/10 Very Good! (1,268 reviews)
"Great stay except for very strong scent in the lobby. Convenient to shopping & dining."

Reviewed on Sep 9, 2025

Novotel Toronto North York
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
The price is $235 total per night from Sep 21 to Sep 22
$235 total
per night
Sep 21 - Sep 22
8.4/10 Very Good! (4,548 reviews)
"Excellent location for traveller arriving by public transport, only 4 subway stops from Union Station, then a 1 minute walk to the Hotel, easily walkable from Union Station also if no luggage. Shops,bars and restaurants all close by as well as all major attractions which are within walkable distance. ..."

Reviewed on Sep 10, 2025

Holiday Inn Toronto Downtown Centre by IHG
Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is $157 total per night from Oct 10 to Oct 11
$157 total
per night
Oct 10 - Oct 11
8.2/10 Very Good! (12,337 reviews)
"Beautiful property with tons of character in the heart of downtown Toronto."

Reviewed on Sep 12, 2025

Chelsea Hotel, Toronto
See all 4,910 properties in Willowdale
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 Willowdale

Mel Lastman Square

You can make plans for a show at Mel Lastman Square on your trip to Toronto. Discover the acclaimed art scene and shops in this walkable area.

Mel Lastman Square

Toronto Centre for the Arts

You can make plans for a show at Toronto Centre for the Arts on your trip to Toronto. Discover the entertainment choices and shops in this walkable area.

Toronto Centre for the Arts

Mitchell Field Arena

Catch an event at Mitchell Field Arena during your trip to Toronto. Discover the entertainment choices and shops in this vibrant area.

Mitchell Field Arena

Things to do

Toronto: Ripley's Aquarium of Canada Entry Ticket

Toronto: Ripley's Aquarium of Canada Entry Ticket

$34
per adult
90% of travellers recommend
Toronto: Ripley's Aquarium of Canada Entry Ticket
Niagara Falls Evening Tour with Boat, Dinner & Illumination Tower

Niagara Falls Evening Tour with Boat, Dinner & Illumination Tower

$87
per adult
94% of travellers recommend
Niagara Falls Evening Tour with Boat, Dinner & Illumination Tower
Toronto: Casa Loma Entry Ticket

Toronto: Casa Loma Entry Ticket

$29
per adult
86% of travellers recommend
Toronto: Casa Loma Entry 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.