South Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in South Side

Price found within the past 48 hours. Click for updated prices.
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Price was CA $2,516, price is now CA $1,478 per person
CA $1,478
per person
Jun 14 - Jun 20
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,852 reviews)
Complementary pastry amazing. Staff was absolutely fantastic…professional and nice.

Reviewed on Apr 9, 2026

The Ned NoMad

The Ned NoMad

5 out of 5
Manhattan
Price was CA $3,083, price is now CA $1,707 per person
CA $1,707
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (119 reviews)
Room was great staff not so good

Reviewed on Feb 15, 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was CA $2,743, price is now CA $1,605 per person
CA $1,605
per person
Jun 26 - Jul 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (1,799 reviews)
Great location for a decent price. The elevator was very slow and had to wait a while for it, the property itself can use a slight upgrade but again for the pricing it was good overall.

Reviewed on Apr 14, 2026

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Price was CA $2,538, price is now CA $1,531 per person
CA $1,531
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,764 reviews)
Great location; Central Park View is a must

Reviewed on Apr 11, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $3,586, price is now CA $2,195 per person
CA $2,195
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Everything is great about this Hotel.

Reviewed on Apr 9, 2026

South Side Hotel Deals

Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street New York NY
Fully refundableReserve now, pay when you stay
The price is CA $302 per night from Apr 19 to Apr 20
CA $302
CA $415 total
Apr 19 - Apr 20
includes taxes & fees
8.2/10 Very Good! (6,676 reviews)
The smell of the bathroom is weird, it didnt smell foul but it smells like old and moist. I had to buy a small space perfume. It was clean, i just didnt like how it smelled. Also the pillows smells like sweat. Staff was amazing. Everyone is so nice.

Reviewed on Apr 14, 2026

Hyatt Grand Central New York
Hotel Edison Times Square

Hotel Edison Times Square

4 out of 5
228 W 47th St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Apr 19 to Apr 20
CA $178
CA $272 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,403 reviews)
The location is amazing! Close to the heart of NYC. Completely breakfast @ carve was good. Received complimentary wine, chips & chocolate! Decent gym too.

Reviewed on Apr 14, 2026

Hotel Edison Times Square
Hyatt Regency Times Square

Hyatt Regency Times Square

4 out of 5
1605 Broadway New York NY
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from May 3 to May 4
CA $251
CA $356 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (925 reviews)
The hotel is mostly very good. It's a great location if you're going to be in Times Square a lot, and it's very clean, the staff are friendly, and overall it's worth the price. However... on our arrival day, two of the three elevators to our floors were not working, though only one was marked as ...

Reviewed on Apr 14, 2026

Hyatt Regency Times Square
See all 12,042 properties in South Side
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.
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Frequently asked questions

How much does a South Side vacation package cost?
From as low as CA $1,478, you can custom build your South Side vacation package. Simply combine flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to South Side?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Choose the combination that suits you and watch your savings grow. We know a package deal is never one-size-fits-all. That's why we offer over 550 airlines and 1,000,000 hotels across the globe, which lets you customize your South Side adventure.
Where should I stay in South Side?
A trip to South Side isn't complete without paying a visit to Montefiore Mount Vernon Hospital, St. Pauls Church National Historic Site and Willsons Woods Park. Spend your evenings close to these popular attractions and make sightseeing easy.
What are the top hotels in South Side?
Modern And Quiet Getaway is one of South Side's top properties. Secure a room here and you'll be able to rest easy knowing you're in excellent hands.
How far in advance should I book my South Side vacation?
It's hard to pick the best time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available up to a year in advance. If you're booking last minute, fear not. Low prices appear from time to time just weeks before departure dates.
What does an Expedia South Side travel package include?
From hotels and flights to rental cars, Expedia can help you create a South Side package that's right for you. Vacationing for a week or longer? Give some thought to a flight, rental car and hotel bundle. If you can only manage a quick getaway, a hotel and flight deal could be what you're after. Tours and activities can be added after you've booked. Our vacation packages make it a breeze to save and plan.
What should I know before booking a South Side travel package?
Booking all the parts of your trip together is one of the best ways to save. Bundle your car rentals, airfares and hotels into one little package. But you're not limited to hotels. Expedia has all types of properties, including vacation rentals such as beachfront villas and short-term homes. Your choices are almost endless!
Can I choose my airline with a South Side Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you certainly can. Just select your favorite carrier and put together your ideal South Side getaway.
If I'm not able to travel, can I cancel my South Side vacation package?
Don't worry if you're rethinking your South Side vacation package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We realize your circumstances can suddenly change, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

Discover the most popular places to visit in South Side

Montefiore Mount Vernon Hospital

Though Montefiore Mount Vernon Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Mount Vernon while you are here.

Montefiore Mount Vernon Hospital
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.