Southside Vacations from $738

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The Latest Southside Vacation Packages

Price found within the past 48 hours. Click for updated prices.

The Waterside Inn

Port Credit

$738

per person

Sep 18 - Sep 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

8.6/10 Excellent! (1,040 reviews)

Room on a lower floor and could hear the noise from the traffic on Lakeshore. Otherwise room was good.

Reviewed on Aug 16, 2026

1 Hotel Toronto

Downtown Toronto

$1,345

per person

Sep 25 - Sep 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (780 reviews)

Everything was absolutely PERFECT! The clean environment, the well kept rooms, the friendly staff and amazing food. Zero complaints and we can’t wait to return to Canada!

Reviewed on Aug 13, 2026

Hotel Riu Plaza Toronto

Downtown Toronto

$1,315

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.4/10 Exceptional! (4,297 reviews)

High quality hotel with all inclusive breakfast it was outstanding the friendliest staff and comfortable beds, excellent service from housekeeping staff. We shall be back!!!

Reviewed on Aug 16, 2026

TOOR Hotel Toronto, part of JdV by Hyatt

Downtown Toronto

$1,126

per person

Sep 18 - Sep 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.4/10 Exceptional! (912 reviews)

The properties in a good location, but many homeless people. The rooms are tiny 10x10 sleeping area, for the price that you pay could be a little larger. Nice tv. Bathroom shower very average. All in all i would only stay there if the price was better.

Reviewed on Aug 16, 2026

Shangri-La Toronto

Downtown Toronto

$2,336

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

9.6/10 Exceptional! (1,324 reviews)

Loved the restaurants and bar

Reviewed on Aug 16, 2026

Where to stay in Southside

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

Saint Jacobs

You'll enjoy the museums and riverfront in Saint Jacobs. You might want to make time for a stop at St. Jacobs Scoolhouse Theatre or Maple Syrup Museum of Ontario.

A train crossing a bridge over a river with a dam in the foreground.

Elmira

Discover the largest Old Order Mennonite community in Canada, with regular buggy sightings and the historic Bandstand in Gore Park. Enjoy the Woolwich Memorial Centre's amenities and explore the Kissing Bridge Trailway for outdoor activities.

A cityscape with autumn foliage, a prominent tall building, and a mix of residential and commercial buildings.

Downtown Kitchener

1 out of top 10 points of interest in this area

While visiting Downtown Kitchener, you might make a stop by sights like Kitchener City Hall and Centre In The Square.

Hespeler

Situated along the Speed River, this industrial-based area offers recreational activities like parks, canoeing, and trails. Explore the Old Town, Fire Hall, Hespeler Library, and Fashion History Museum.

East Galt

While there might not be top attractions in East Galt, you can explore the larger area and discover places like McDougall Cottage and Dunfield Theatre Cambridge.

Southside Hotel Deals

Quality Inn

2899 King St E Kitchener ON

Fully refundableReserve now, pay when you stay

$60 nightly

$70 total

Sep 13 - Sep 14

Total with taxes and fees

8.2/10 Very Good! (1,734 reviews)

"Nothing to dislike.!"

Reviewed on Aug 16, 2026

The Walper Hotel, part of JdV by Hyatt

20 Queen St S. Kitchener ON

Fully refundableReserve now, pay when you stay

$110 nightly

$129 total

Aug 23 - Aug 24

Total with taxes and fees

9.2/10 Wonderful! (1,004 reviews)

"⭐⭐⭐⭐⭐ Amazing Last‑Minute Stay — Clean, Friendly, and Perfectly Located I booked this hotel last minute and it ended up being one of the best overnight stays I’ve had downtown. The room was spotless, the staff were genuinely great, and the amenities were impressive for the price. There’s an awesome ..."

Reviewed on Aug 16, 2026

Crowne Plaza Kitchener-Waterloo by IHG

105 King St E Kitchener ON

Fully refundable

$102 nightly

$119 total

Aug 23 - Aug 24

Total with taxes and fees

8.4/10 Very Good! (1,678 reviews)

"An older hotel, with very narrow hallways in the area I was staying. Elevators were not well marked in the hallways leaving my room. On the last day of a 5 night stay I found a set of elevators much closer to my room - the sign in my hallway pointed in the opposite direction for elevators. If you ..."

Reviewed on Aug 15, 2026

See all 578 properties in Southside

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.