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.
Loews Regency New York Hotel
Manhattan
Price was CA $3,110, price is now CA $1,845 per person
CA $1,845
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Staff were very accomodating and looked after my family well during our stay. Nothing was too difficult for them.
Reviewed on Jan 17, 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 1 day 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 1 day 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
Arthouse Hotel New York City
Manhattan
Price was CA $2,247, price is now CA $1,410 per person
CA $1,410
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,678 reviews)
Hip boutique hotel with an industrial cozy vibe. Rooms are sumple but have everything you need. The libby bar and cafe are nice. Attached to Serafina restaurant. Great lication overall and parking across the street.
Reviewed on Feb 6, 2026
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is CA $215 per night from Feb 16 to Feb 17
CA $215
CA $246 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 $203 per night from Mar 10 to Mar 11
CA $203
CA $271 total
Mar 10 - Mar 11
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.
