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.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,469, price is now CA $869 per person
CA $869
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,565 reviews)
The property was very clean and

Reviewed on Apr 8, 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

The William Vale

The William Vale

5 out of 5
Price was CA $2,449, price is now CA $1,503 per person
CA $1,503
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,026 reviews)
Great calm and well Located place to stay. Amazing view and dinning options.

Reviewed on Apr 3, 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Price was CA $3,439, price is now CA $2,118 per person
CA $2,118
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! (1,003 reviews)
Great staff, amazing lunch and breakfast

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 $317 per night from Apr 26 to Apr 27
CA $317
CA $432 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (6,664 reviews)
Great location an update rooms. Would recommend.

Reviewed on Apr 13, 2026

Hyatt Grand Central New York
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
811 7th Ave New York NY
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from Apr 19 to Apr 20
CA $289
CA $392 total
Apr 19 - Apr 20
includes taxes & fees
7.4/10 Good! (7,568 reviews)
Great

Reviewed on Apr 13, 2026

Sheraton New York Times Square Hotel
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 $179 per night from Apr 19 to Apr 20
CA $179
CA $273 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,392 reviews)
Clean, safe, and a wonderful room for our family stay in NYC. Staff was very helpful and we really enjoyed the breakfast options that were included. The staff even gave us four vouchers for everyday since we had four in our party.

Reviewed on Apr 12, 2026

Hotel Edison Times Square
See all 12,029 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.
All Inclusive Vacations
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Frequently asked questions

How much does a South Side vacation package cost?
From as low as CA $869, 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.