
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.

The Inn At Fox Hollow Hotel
Price was CA $1,179, price is now CA $697 per person
CA $697
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Very large room, well maintained hotel, friendly helpful staff.
Reviewed on Aug. 25, 2025

1 Hotel Brooklyn Bridge
Price was CA $3,736, price is now CA $2,074 per person
CA $2,074
per person
Oct 28 - Oct 31
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.
Reviewed on Aug. 21, 2025

The Luxury Collection Hotel Manhattan Midtown
Manhattan
Price was CA $1,798, price is now CA $1,101 per person
CA $1,101
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Great location, complimentary water which saved us a lot of money on bottled water!
Front desk hooked us up with an upgrade. We requested to have all snacks and drinks removed from our son's room and they didn't do it. He got into the snacks and we were charged $160 super annoying, we knew he would get into the snacks and would have appreciated them doing us a solid by removing the $20 gummy bears
Reviewed on Aug. 17, 2025

Hyatt Regency Jersey City on the Hudson
Downtown Jersey City
Price was CA $1,572, price is now CA $974 per person
CA $974
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,466 reviews)
This hotel had a beautiful view of the Hudson and the city. It was super convenient to the PATH station and parking garage.
Reviewed on Aug. 25, 2025

Hotel St. James
Manhattan
Price was CA $1,256, price is now CA $821 per person
CA $821
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (6,263 reviews)
The hotel was good and the staff were so nice. I would go again!
Reviewed on Aug. 27, 2025
Southold Hotel Deals

The Shoals Suites and Slips
61600 Main Rd, Southold, NY
The price is CA $512 per night from Sep 3 to Sep 4
CA $512
CA $620 total
Sep 3 - Sep 4
includes taxes & fees
9.4/10 Exceptional! (192 reviews)
"The hotel was lovely"
Reviewed on Aug. 9, 2025

Greenview Inn Riverhead
1433 W Main St, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Sep 2 to Sep 3
CA $138
CA $158 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (704 reviews)
"A"
Reviewed on Aug. 24, 2025

The Atlantic Hotel
1655 County Road 39, Southampton, NY
The price is CA $223 per night from Sep 21 to Sep 22
CA $223
CA $289 total
Sep 21 - Sep 22
includes taxes & fees
7/10 Good! (915 reviews)
"Nice staff and the hotel is fine."
Reviewed on Aug. 24, 2025
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

From Mattituck: North Fork Area Bike Tour with Food Tasting
CA $191
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.