Southside Vacations from $546
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Southside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
One King West Hotel & Residence
Downtown Toronto
Save 100% on your flight
Price was $846, price is now $546 per person
$546
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (8,020 reviews)
Poor housekeeping. No cold water in the room at arrival
Reviewed on Jun 30, 2026
Hotel Riu Plaza Toronto
Downtown Toronto
Price was $1,343, price is now $859 per person
$859
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (3,788 reviews)
There's no parking available, so if driving, look for parking locations nearby at a premium.
There's no hot tub available to unwind after a long day of walking around the city.
Breakfast was excellent for all the meat eaters but lacking for vegetarians, when bringing this up to one of the managers he said they try to rotate but that doesn't help. Unlike the RIU in Panamá, the Breakfast there is awesome, Toronto needs work
Reviewed on Jul 1, 2026
1 Hotel Toronto
Downtown Toronto
Save 100% on your flight
Price was $1,552, price is now $1,021 per person
$1,021
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (748 reviews)
A wonderful experience from start to finish!
Reviewed on Jun 30, 2026
Finlay House Bed and Breakfast Niagara - on - the - Lake
Old Town Historic District
Price was $1,302, price is now $867 per person
$867
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (237 reviews)
We had a wonderful stay & Woolf he happy to stay again. Yvonne was a gracious host, serving a lovely hot breakfast each morning. I was traveling with my aunt who had some medically related needs and Yvonne made it clear she was there to help, gave us extra supplies and towels and made us feel so very welcome. She also shared her local knowledge of the area.
The inn itself was recently redecorated with lovely furnishings, art, and beautiful wallpapers. Our room (Bernard Shaw Room) was spacious and the bed was so comfortable! My aunt and I shared the oversized king that has a memory foam mattress which prevents one from noticing movement of the other - we slept like rocks!
The only improvement I might suggest would be better internet connection, but I wasn’t there to work so it was okay.
Beautifully done, quaint/updated, comfortable, great breakfasts, excellent host!
Reviewed on Jun 26, 2026
Sterling Inn & Spa - an Ontario's Finest Inn
Clifton Hill
Price was $780, price is now $559 per person
$559
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (2,418 reviews)
They gave me an upgraded suite for our one-night stay. Probably the best room I’ve ever stayed in. Breakfast served to your room was included, and was excellent. Parking was reasonable for the area, but was a dollar more than I was quoted ($18CAD VS $17CAD). Not a big deal. Would definitely recommend it and would stay again!
Reviewed on Jul 1, 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.
Southside Hotel Deals
Quality Inn
2899 King St E Kitchener ON
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $75 total per night from Jul 19 to Jul 20
$75 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (1,668 reviews)
"Breakfast was varied, well thought out and delicious."
Reviewed on Jun 29, 2026
Crowne Plaza Kitchener-Waterloo by IHG
105 King St E Kitchener ON
Fully refundable
$103 nightly
The price is $121 total per night from Jul 30 to Jul 31
$121 total
Jul 30 - Jul 31
Total with taxes and fees
8.4/10 Very Good! (1,643 reviews)
"the hotel is in an older building. staff were terrific. amenities were great. loved bowling in the basement! the games room was a nice surprise."
Reviewed on Jun 30, 2026
The Walper Hotel, part of JdV by Hyatt
20 Queen St S. Kitchener ON
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Jul 6 to Jul 7
$129 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (1,011 reviews)
"A big shout out to all the staff working at the front desk. They could not have been more professional. I noted on a pad a few tweaks to the room we stayed in I thought the management should consider. Normally, this would be a fool’s errand and met with a polite thank you. But not here. The person ..."
Reviewed on Jun 30, 2026
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.
Things to do
Guided Historical and Cultural Tour in Downtown Paris, ON Canada
$23
per adult
Self Guided Driving Taste Tour - Brantford & Paris, ON - Private
$91
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.