Southold Vacations from ￥719,223
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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.
The Evelyn Hotel
Manhattan
Price was ￥1,200,774, price is now ￥719,223 per person
￥719,223
per person
Jul 6 - Jul 10
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (1,307 reviews)
Fantastic location in nomad, staff were great and the hotel felt small and intimate!
Reviewed on May 13, 2026
The Lombardy Hotel
Manhattan
Price was ￥1,216,073, price is now ￥735,168 per person
￥735,168
per person
Jul 6 - Jul 10
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (1,448 reviews)
The sq footage for a hotel room in Manhattan, especially in such a convenient location, is quite phenomenal. Rooms are dated but impeccably clean and well maintained.
Did not find an AC control in the room and it was a little warm. The kitchen is well equipped and a great bonus I'd imagine for those travelling with a family
Reviewed on May 15, 2026
The Prince Kitano New York
Manhattan
Price was ￥1,262,887, price is now ￥764,260 per person
￥764,260
per person
Jul 6 - Jul 10
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.4/10 Exceptional! (2,254 reviews)
Always immaculate, friendly, peaceful - a real refuge.
Reviewed on May 7, 2026
Park South Hotel, part of JdV by Hyatt
Manhattan
Price was ￥1,219,990, price is now ￥739,909 per person
￥739,909
per person
Jul 6 - Jul 10
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
My bedroom had a view on the so-called courtyard which was just a sordid I’m
Reviewed on May 6, 2026
Find the Best Southold Vacation Packages
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is ￥38,431 per night from May 31 to Jun 1
￥38,431
￥47,875 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (269 reviews)
Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend.
Reviewed on May 5, 2026
Vine & Sand
47100 New York 25 Southold NY
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!
Reviewed on Mar 22, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is ￥12,760 per night from May 19 to May 20
￥12,760
￥14,674 total
May 19 - May 20
includes taxes & fees
8/10 Very Good! (1,005 reviews)
Great place very inexpensive.
Reviewed on May 16, 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
￥30,121
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.
