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 ฿7,814 per night from 26 May to 27 May
฿7,814
฿9,734 total
26 May - 27 May
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 5 May 2026
Vine & Sand
47100 New York 25 Southold NY
The price is ฿11,636 per night from 13 May to 14 May
฿11,636
฿13,294 total
13 May - 14 May
includes taxes & fees
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!
Reviewed on 22 Mar 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is ฿5,121 per night from 17 May to 18 May
฿5,121
฿5,851 total
17 May - 18 May
includes taxes & fees
9.6/10 Exceptional! (496 reviews)
Great for dogs - huge fenced yard
Reviewed on 11 May 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
฿5,747
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
฿10,824
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.
