Southold Packages (Flight + Hotel)
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Top hotels in Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is ฿5,332 per night from 4 Feb to 5 Feb
฿5,332
฿6,092 total
4 Feb - 5 Feb
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 22 Jan 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 19 Jan 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿4,534 per night from 17 Feb to 18 Feb
฿4,534
฿6,079 total
17 Feb - 18 Feb
includes taxes & fees
8.4/10 Very Good! (608 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 10 Jan 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.
Popular places to visit
Sparkling Pointe
You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.
What to do in Southold
Private Luxury Wine Tours of Long Island Pindar Winery
฿5,594
per adult
Long Island Wine Tour North Fork Sights Bites Flights Half Day PM
฿10,535
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.
