South Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to CA $775 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in South Side

Price found within the past 48 hours. Click for updated prices.
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 26 - Aug. 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,940 reviews)
The hotel was nice, clean and modern. The carpet in the hallway is very plush. I would definitely stay again.

Reviewed on Jun. 6, 2024

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
Aug. 18 - Aug. 25
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
8.8/10 Excellent! (2,453 reviews)
They don’t put water in the room anymore. The explanation they gave for why was ridiculous

Reviewed on Jun. 6, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Aug. 18 - Aug. 25
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (547 reviews)
the incredible location I had a wonderful experience, want to come back

Reviewed on May 28, 2024

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 18 - Aug. 25
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9.8/10 Exceptional! (1,011 reviews)
Great for biz travelers!

Reviewed on Jun. 5, 2024

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Aug. 30 - Sep. 3
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.6/10 Excellent! (1,004 reviews)
This place is perfect

Reviewed on Jun. 4, 2024

South Side Hotel Deals

The Manhattan at Times Square Hotel
The Manhattan at Times Square Hotel
4 out of 5
790 7th Ave, New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jun. 16 to Jun. 17
CA $190
CA $283 total
includes taxes & fees
Jun 16 - Jun 17
5.6/10 (4,320 reviews)
"Nice hotel, great location."

Reviewed on Jun. 5, 2024

The Manhattan at Times Square Hotel
Hyatt Grand Central New York
Hyatt Grand Central New York
4 out of 5
109 East 42nd Street, at Grand Central Terminal, New York, NY
Fully refundable
The price is CA $220 per night from Jun. 9 to Jun. 10
CA $220
CA $320 total
includes taxes & fees
Jun 9 - Jun 10
7.8/10 Good! (3,523 reviews)
"The hotel is good 42nd st in New York is just sketchy outside the front door just part of the New York charme I guess!"

Reviewed on Jun. 5, 2024

Hyatt Grand Central New York
The New Yorker A Wyndham Hotel
The New Yorker A Wyndham Hotel
4 out of 5
481 Eighth Ave., New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jun. 9 to Jun. 10
CA $218
CA $300 total
includes taxes & fees
Jun 9 - Jun 10
8/10 Very Good! (4,535 reviews)
"Great location and good service, room is small though"

Reviewed on Jun. 5, 2024

The New Yorker A Wyndham Hotel
See all 9,535 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

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Family Vacations

Frequently asked questions

How much does a South Side vacation package cost?
From as low as CA $811, 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

Image for St. Paul's Church National Historic Site

St. Paul's Church National Historic Site

Learn about the local history of Mount Vernon when you take a trip to St. Paul's Church National Historic Site. Amble around this vibrant area's picturesque gardens or experience its acclaimed art scene.

St. Paul's Church National Historic Site
Image for Grace Baptist Church

Grace Baptist Church

You can find out about the history of Mount Vernon when you stop by Grace Baptist Church. Experience the acclaimed art scene and fascinating museums in this vibrant area.

Grace Baptist Church
Image for St. Paul's Church National Historic Site

St. Paul's Church National Historic Site

Learn about the local history of Mount Vernon when you take a trip to St. Paul's Church National Historic Site. Amble around this family-friendly area's picturesque gardens or experience its acclaimed art scene.

St. Paul's Church National Historic Site

Other vacations you might like

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