Southold Vacation Packages
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Your Southold Vacation
The coastal scenery and rich history are just the beginning of the things Southold has going for it. Experience the very best of this interesting city your way with a customized Southold vacation package. 67 Steps Beach, Raphael Winery and Railroad Museum of Long Island are just some of the many sights worth checking out during your trip to Southold. A few quick clicks is all it takes to put together your ideal Southold vacation on Expedia.
Top Southold Vacation Deals
Price found within the past 48 hours. Click for updated prices.
2 bedroom luxury Empire State VIEW
Manhattan
Price was CA $3,975, price is now CA $2,103 per person
CA $2,103
per person
Jul 10 - Jul 12
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on Mar 19, 2026
New York Marriott Marquis
Manhattan
Price was CA $2,403, price is now CA $1,298 per person
CA $1,298
per person
Jul 1 - Jul 5
found 2 hours ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.4/10 Exceptional! (4,384 reviews)
We’ll definitely definitely be staying there again! Very beautiful hotel, and it has a Starbucks on the first floor!
Reviewed on May 7, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
Price was CA $2,877, price is now CA $1,762 per person
CA $1,762
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,468 reviews)
Every thing was good
Reviewed on May 8, 2026
Hotel Riu Plaza New York Times Square
Manhattan
Price was CA $2,852, price is now CA $1,748 per person
CA $1,748
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,979 reviews)
I assume breakfast was good because there was always a line.
Reviewed on May 9, 2026
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is CA $298 per night from May 21 to May 22
CA $298
CA $375 total
May 21 - May 22
includes taxes & fees
9.4/10 Exceptional! (268 reviews)
Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend.
Reviewed on May 5, 2026
Vine & Sand
47100 New York 25 Southold NY
The price is CA $444 per night from May 13 to May 14
CA $444
CA $507 total
May 13 - May 14
includes taxes & fees
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!
Reviewed on Mar 22, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is CA $864 per night from May 15 to May 16
CA $864
CA $1,104 total
May 15 - May 16
includes taxes & fees
8.6/10 Excellent! (645 reviews)
Beautiful place to stay on a special getaway
Reviewed on May 7, 2026
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.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
CA $261
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
