South Side Vacations from ￥214,625

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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

The Latest South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The William Vale

The William Vale

5 out of 5
Price was ￥320,990, price is now ￥214,625 per person
￥214,625
per person
Feb 6 - Feb 11
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (NYC)
17.6/10 Exceptional! (1,002 reviews)
The 2 concierges Samantha & Daniella -were fabulous! So appreciative!

Reviewed on Nov 22, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥563,092, price is now ￥344,590 per person
￥344,590
per person
Feb 6 - Feb 11
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (NYC)
19.2/10 Exceptional! (159 reviews)
What an incredibly beautiful place this hotel is! Staff cannot do enough and made ourspecial anniversary stay truly perfect..the hotel is beautifully decorated and immaculate throughout. Cannot recommend this enough

Reviewed on Nov 17, 2025

Faena New York

Faena New York

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥732,992, price is now ￥462,774 per person
￥462,774
per person
Feb 3 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
No reviews
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was ￥383,337, price is now ￥248,267 per person
￥248,267
per person
Dec 30 - Jan 5
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newark Liberty Intl. Airport (EWR)
16.8/10 Exceptional! (1,565 reviews)
Good Hotel for business travelers & tourists for Manhattan, NYC region without cars.

Reviewed on Nov 20, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥480,108, price is now ￥320,384 per person
￥320,384
per person
Feb 6 - Feb 11
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (NYC)
18/10 Exceptional! (1,001 reviews)
Loved all the plants in this place and around it. Super chill vibe. Very clean. Front desk staff very kind and helpful!

Reviewed on Nov 23, 2025

South Side Hotel Deals

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 ￥28,095 per night from Nov 30 to Dec 1
￥28,095
￥39,090 total
Nov 30 - Dec 1
includes taxes & fees
7.4/10 Good! (5,583 reviews)
The room was very clean, and the hotel is located in a great location for walking to the theater, restaurants, and even Penn Station. HOWEVER, the elevator system is horrendous!! Large groups gather in front of the elevator that has been designated to take you to your floor, so we often had to wait ...

Reviewed on Nov 24, 2025

Sheraton New York Times Square Hotel
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street New York NY
The price is ￥34,910 per night from Nov 29 to Nov 30
￥34,910
￥47,785 total
Nov 29 - Nov 30
includes taxes & fees
8/10 Very Good! (6,360 reviews)
Very

Reviewed on Nov 24, 2025

Hyatt Grand Central New York
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
145 W 44th St New York NY
Fully refundableReserve now, pay when you stay
The price is ￥21,177 per night from Nov 30 to Dec 1
￥21,177
￥30,252 total
Nov 30 - Dec 1
includes taxes & fees
7.6/10 Good! (6,115 reviews)
Great staff Danny was great

Reviewed on Nov 24, 2025

Millennium Hotel Broadway Times Square
See all 10,752 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.

Frequently asked questions

How much does a South Side vacation package cost?
From as low as ￥214,625, 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.