Southold Holidays
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Southold Holiday
Our pick of the best Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is NZ$469 per night from 26 May to 27 May
NZ$469
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 NZ$812 per night from 26 May to 27 May
NZ$812
26 May - 27 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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is NZ$154 per night from 19 May to 20 May
NZ$154
19 May - 20 May
includes taxes & fees
8/10 Very Good! (1,009 reviews)
"We have been coming here for years and it is the best it’s ever been! Staff is friendly and accommodating. The rooms have been renovated and clean."
Reviewed on 17 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.
Discover the most popular places to visit in Southold
Mattebella Vineyards
You can enjoy a tasting or tour at Mattebella Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
NZ$321
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.
