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 $4,200 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
Price found within the past 48 hours. Click for updated prices.
  • Hallway
    Jul 17 - Jul 20

    The Wayne Inn + Flight

    Wayne
    3 nights
    2.0 star property
    7.0/10 - Good (300 reviews)
    Roundtrip • Toronto (YYZ) - New York (JFK)
    YYZ - JFK • Nonstop JFK - YYZ • Nonstop
    CA $1,578
    CA $857
    per traveller
    found 6 hours ago
    The Wayne Inn
  • Suite, 1 Bedroom (Skyline)
    Aug 11 - Aug 18

    1 Hotel Brooklyn Bridge + Flight

    Brooklyn
    7 nights
    5.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "The hotel is beautiful and in unic place the stuff provides an outstanding service starting from valley parking, at front desk, at pool, in restaurants! It was my husband’s birthday. We got Champagne and sweets! Wish to come again. Highly recomended."
    Reviewed June 1, 2026
    Roundtrip • Vancouver (YVR) - New York (EWR)
    YVR - EWR • Nonstop EWR - YVR • Nonstop
    CA $8,121
    CA $4,791
    per traveller
    found 1 day ago
    1 Hotel Brooklyn Bridge
  • Front of property
    Aug 14 - Aug 19

    Hotel St. James + Flight

    Manhattan
    5 nights
    3.0 star property
    8.8/10 - Excellent (7,416 reviews)
    "Prime location, but a very simple hotel, small rooms, no fridge in standard queen rooms, no views, no place to put toiletries in the bathroom. Clean. You are paying for the location, basically. Staff was very friendly"
    Reviewed June 4, 2026
    Roundtrip • Hamilton (YHM) - New York (EWR)
    YHM - EWR • 1 stop EWR - YHM • 1 stop
    CA $1,701
    CA $1,056
    per traveller
    found 1 day ago
    Hotel St. James
  • Outdoor pool
    Aug 17 - Aug 21

    Topping Rose House + Flight

    Bridgehampton
    3 nights
    4.5 star property
    9.0/10 - Wonderful (152 reviews)
    "Amazing"
    Reviewed May 29, 2026
    Roundtrip • Vancouver (YVR) - New York (LGA)
    YVR - LGA • 1 stop JFK - YVR • 1 stop
    CA $7,353
    CA $4,567
    per traveller
    found 6 hours ago
    Topping Rose House
  • Lobby lounge
    Aug 6 - Aug 9

    The Towers at Lotte New York Palace + Flight

    Manhattan
    3 nights
    5.0 star property
    9.2/10 - Wonderful (679 reviews)
    "Very good"
    Reviewed May 23, 2026
    Roundtrip • Toronto (YYZ) - New York (JFK)
    YYZ - JFK • Nonstop JFK - YYZ • Nonstop
    CA $3,549
    CA $2,265
    per traveller
    found 1 day ago
    The Towers at Lotte New York Palace

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
The price is CA $346 per night from Jul 1 to Jul 2
CA $346
CA $466 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (7,096 reviews)
"Popped in for a first time visit to New York for an event. The place was affordable for being downtown. Was right at Grand Central station so wherever we wanted to go was easily accessible by the Subways. Check in was easy and our room wasn’t huge by any means but that’s not most important to me. ..."

Reviewed on Jun 5, 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 $207 per night from Jun 14 to Jun 15
CA $207
CA $306 total
Jun 14 - Jun 15
includes taxes & fees
8.6/10 Excellent! (5,636 reviews)
"New favorite hotel in NYC. Polite, helpful staff. Quiet, clean, well appointed room. In the heart of the Theatre district."

Reviewed on Jun 4, 2026

Hotel Edison Times Square
Empire Hotel

Empire Hotel

4 out of 5
44 W 63rd St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $242 per night from Jun 28 to Jun 29
CA $242
CA $314 total
Jun 28 - Jun 29
includes taxes & fees
7.6/10 Good! (6,840 reviews)
"Enjoyed the stay however the keys to the room wasn’t working very well and took many try’s to get into the room. However very clean and staff was nice and enjoyed the rooftop!"

Reviewed on Jun 5, 2026

Empire Hotel
See all 11,955 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 , 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.