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
The Ned NoMad
OYO Times Square
Park Lane New York
1 Hotel Central Park

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
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.

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

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