Southold Vacations from ￥426,952
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 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.
Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was ￥667,353, price is now ￥426,952 per person
￥426,952
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,931 reviews)
Everything was wonderful from location to breakfast to staff.
Reviewed on Mar 29, 2026
Loews Regency New York Hotel
Manhattan
Save 100% on your flight
Price was ￥1,932,520, price is now ￥1,202,112 per person
￥1,202,112
per person
Jun 8 - Jun 15
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,002 reviews)
Great location nice room and bar/restaurant
Reviewed on Mar 28, 2026
Placemakr Wall Street
Manhattan
Save 100% on your flight
Price was ￥1,202,545, price is now ￥778,222 per person
￥778,222
per person
Jun 8 - Jun 15
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (890 reviews)
Clean room very spacious.
Reviewed on Mar 23, 2026
INNSiDE by Meliá New York Nomad
Manhattan
Save 100% on your flight
Price was ￥1,140,840, price is now ￥795,285 per person
￥795,285
per person
Jun 8 - Jun 15
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (2,221 reviews)
The room was very clean, the staff was right there when you needed them, the restaurant staff was great.
Reviewed on Mar 29, 2026
The Fifth Avenue Hotel
Manhattan
Save 100% on your flight
Price was ￥1,075,196, price is now ￥756,284 per person
￥756,284
per person
Jun 8 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (196 reviews)
Absolutely everything. Amazingly appointed room, very friendly stafff.
Reviewed on Mar 1, 2026
Find the Best Southold Vacation Packages
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is ￥23,068 per night from Apr 23 to Apr 24
￥23,068
￥30,362 total
Apr 23 - Apr 24
includes taxes & fees
9.4/10 Exceptional! (250 reviews)
Clean, spacious and thoughtful room amenities. Close by to town and great restaurants.
Reviewed on Mar 23, 2026
Vine & Sand
47100 New York 25 Southold NY
The price is ￥61,510 per night from Apr 5 to Apr 6
￥61,510
￥70,277 total
Apr 5 - Apr 6
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
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is ￥34,054 per night from Mar 30 to Mar 31
￥34,054
￥41,928 total
Mar 30 - Mar 31
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Enjoyable stay.
Reviewed on Mar 28, 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
￥29,467
per adult
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.