Southold Holidays

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The Annual Holiday Sale

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Southold Holiday

Our pick of the best Southold Hotel Deals

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is NZ$295 per night from 18 Feb to 19 Feb
NZ$295
18 Feb - 19 Feb
includes taxes & fees
9.4/10 Exceptional! (239 reviews)
Room was great. Clean and comfortable. Glad I found this place and will be back.

Reviewed on 22 Jan 2026

The Shoals Suites and Slips
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is NZ$329 per night from 18 Mar to 19 Mar
NZ$329
18 Mar - 19 Mar
includes taxes & fees
8.4/10 Very Good! (610 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

Sound View Greenport
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is NZ$401 per night from 24 Feb to 25 Feb
NZ$401
24 Feb - 25 Feb
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Great amenities, Beautiful view, and Caring Staff.

Reviewed on 12 Feb 2026

Water's Edge Resort & Spa
See all 4,326 properties in Southold
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.

Mattebella Vineyards

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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.