South Side Vacations from $223

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Your South Side Vacation

Your next great adventure is calling with a vacation package to South Side. Entertainment, relaxation and nonstop great times — you're bound to find it in this neighborhood. Wondering what to see and do during your trip to South Side? Nearby attractions such as St. Pauls Church National Historic Site, Grace Baptist Church and Willsons Woods Park are good places to start. Expedia can put your travel plans into action. Book your perfect South Side vacation today.

The Latest South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Price was $452, price is now $223 per person
$223
per person
Jan 30 - Feb 3
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.4/10 Very Good! (1,001 reviews)
Beautiful place to be

Reviewed on Nov 20, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $631, price is now $297 per person
$297
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.6/10 Excellent! (2,613 reviews)
The location was ideal for our stay. The restaurant food was amazing.

Reviewed on Nov 22, 2025

Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $911, price is now $440 per person
$440
per person
Feb 5 - Feb 11
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7.8/10 Good! (80 reviews)
I wish there was a coffee maker in the room, also the TV was very small and angled away from the bed. It was super quiet, which was great, and very clean and warm.

Reviewed on Nov 16, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $639, price is now $312 per person
$312
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (2,008 reviews)
There were so many broken amenities, hair dryer, sink, remote control and even the key access reader. Staff members were super friendly though, they need some maintenance done.

Reviewed on Nov 26, 2025

Oheka Castle Hotel & Estate

Oheka Castle Hotel & Estate

3.5 out of 5
Price was $2,272, price is now $1,129 per person
$1,129
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
9/10 Wonderful! (645 reviews)
Charming location, huge rooms. Restaurant only okay.

Reviewed on Nov 3, 2025

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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
$251 nightly
The price is $291 total per night from Nov 30 to Dec 1
$291 total
Nov 30 - Dec 1
Total with taxes and fees
7.4/10 Good! (5,620 reviews)
Location was incredible

Reviewed on Nov 27, 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
$285 nightly
The price is $330 total per night from Nov 30 to Dec 1
$330 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (6,370 reviews)
I was great, the staff wasn’t the best overall in multiple ways but everything else was tip top so I definitely feel like it was worth its price and Im happy

Reviewed on Nov 25, 2025

Hyatt Grand Central New York
Hotel St. James

Hotel St. James

2.5 out of 5
109 W. 45TH ST. New York NY
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $162 total per night from Nov 30 to Dec 1
$162 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (6,606 reviews)
Wonderful. Perfectly located.

Reviewed on Nov 27, 2025

Hotel St. James
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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.
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Discover the most popular places to visit in South Side

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