Southold Vacations from ₩1,733,006
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- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Southold Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Ink 48 Hotel
Manhattan
Save 100% on your flight
Price was ₩2,599,090, price is now ₩1,733,006 per person
₩1,733,006
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to New York (NYC)
8.4/10 Very Good! (1,438 reviews)
Great hotel, great staff but wow the roof top bar next to the hotel, very loud music till 4am in the morning not good when you have a full day ahead.
Reviewed on Nov 8, 2025
INNSiDE by Meliá New York Nomad
Manhattan
Save 100% on your flight
Price was ₩3,366,295, price is now ₩2,150,414 per person
₩2,150,414
per person
Dec 22 - Dec 27
found 3 hours ago
Roundtrip flight included
Port of Spain (POS) to New York (NYC)
9.2/10 Wonderful! (2,030 reviews)
Super friendly staff. Great location. We had an issue with the bedding, and they solved in minutes.
Reviewed on Nov 12, 2025
Interfaith 21
Manhattan
Save 100% on your flight
Price was ₩2,809,188, price is now ₩1,824,013 per person
₩1,824,013
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to New York (NYC)
8.4/10 Very Good! (24 reviews)
We wanted a clean room to sleep. It was quite clean. Out expectations were met. Staff was very nice and helpful. Shared bathroom was not a problem.
Reviewed on Oct 12, 2025
Hotel Beacon
Manhattan
Save 100% on your flight
Price was ₩5,493,496, price is now ₩3,660,706 per person
₩3,660,706
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Port of Spain (POS) to New York (NYC)
9.4/10 Exceptional! (1,316 reviews)
Lovely large clean room with a small kitchenette Great neighborhood with so many restaurant options within walking distance. The subway is 3 blocks away. The staff was very friendly.
Reviewed on Nov 12, 2025
Hotel Seville Nomad, in the Unbound Collection by Hyatt
Manhattan
Price was ₩3,787,778, price is now ₩2,543,108 per person
₩2,543,108
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Port of Spain (POS) to New York (NYC)
8.8/10 Excellent! (1,140 reviews)
Nice hotel. Clean, good location, helpful staff. Got lucky with an unusually large room for our 3 night stay
Reviewed on Nov 10, 2025
Find the Best Southold Vacation Packages
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd, Southold, NY
The price is ₩271,099 per night from Nov 16 to Nov 17
₩271,099
₩346,270 total
Nov 16 - Nov 17
includes taxes & fees
9.4/10 Exceptional! (220 reviews)
This was a stunning place to stay in all respects. The large room was wonderrful. Thank you!
Reviewed on Nov 8, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,006 reviews)
The room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...
Reviewed on Nov 3, 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
The price is ₩285,898 per night from Dec 14 to Dec 15
₩285,898
₩398,521 total
Dec 14 - Dec 15
includes taxes & fees
8.4/10 Very Good! (586 reviews)
Staff was amazing , room clean view phenomenal
Reviewed on Nov 5, 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.
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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.
