Southold Holidays from AU$3,018

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Your Southold Holiday

The coastal scenery and rich history are just the beginning of the things Southold has to offer. Discover the best of this captivating city your way with a personalised Southold holiday package. If taking in sights is part of the programme during your trip to Southold, swing by leading attractions like 67 Steps Beach, Pindar Vineyards and Kontokosta Winery. Don't put off your visit to this city any longer. Your dream Southold holiday is just a few clicks away with Expedia.

The Latest Southold Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Hotel Riu Plaza New York Times Square
WestHouse New York
1 Hotel Central Park
The Langham, New York, Fifth Avenue

Southold Holiday

Southold Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
5,700
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
67 Steps Beach, Macari Vineyards and Pindar Vineyards

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 AU$305 per night from 29 Apr to 30 Apr
AU$305
29 Apr - 30 Apr
includes taxes & fees
9.4/10 Exceptional! (261 reviews)
The room was spacious. I’m very clean. I was very impressed. Location easy to get in and out of highly recommend.

Reviewed on 14 Apr 2026

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
The price is AU$540 per night from 22 Apr to 23 Apr
AU$540
22 Apr - 23 Apr
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

Vine & Sand
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 AU$423 per night from 26 Apr to 27 Apr
AU$423
26 Apr - 27 Apr
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Front desk staff were amazing! The bar staff were very attentive and friendly. Rooms are clean, but definitely dated.

Reviewed on 13 Apr 2026

Water's Edge Resort & Spa
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

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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.