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.
Hotel St. James
Manhattan
Price was CA $1,289, price is now CA $836 per person
CA $836
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
The best place to stay on a budget if you’re planning to see Broadway shows. I’ve already reserved The St. James for my trip in April.
Reviewed on Feb 6, 2026
1 Hotel Central Park
Manhattan
Price was CA $3,267, price is now CA $2,010 per person
CA $2,010
per person
Apr 25 - Apr 29
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby.
Reviewed on Feb 2, 2026
The Fifth Avenue Hotel
Manhattan
Price was CA $3,505, price is now CA $2,194 per person
CA $2,194
per person
Apr 25 - Apr 29
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (159 reviews)
Staff were lovely, helpful and pleasant. Turndown service way too late, though—9:45 might catch some guests sleeping.
Reviewed on Jan 3, 2026
1 Hotel Brooklyn Bridge
Price was CA $2,254, price is now CA $1,469 per person
CA $1,469
per person
Apr 25 - Apr 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
The entire stay was exceptional! From the point of entry to departure 10/10
Reviewed on Jan 29, 2026
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is CA $216 per night from Feb 16 to Feb 17
CA $216
CA $247 total
Feb 16 - Feb 17
includes taxes & fees
9.4/10 Exceptional! (238 reviews)
Room was great. Clean and comfortable. Glad I found this place and will be back.
Reviewed on Jan 22, 2026
Vine & Sand
47100 New York 25 Southold NY
9.6/10 Exceptional! (15 reviews)
Vine + Sand was wonderful. The hosts were so friendly and it was close to many wineries.
Reviewed on Jan 19, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is CA $204 per night from Mar 9 to Mar 10
CA $204
CA $272 total
Mar 9 - Mar 10
includes taxes & fees
8.4/10 Very Good! (609 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...
Reviewed on Jan 10, 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.
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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.
