Southold Holidays from AU$2,691
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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 New York Times Square
Manhattan
Price was AU$4,092, price is now AU$2,691 per person
AU$2,691
per person
14 Aug - 21 Aug
found 24 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (3,026 reviews)
This was my first time traveling to NYC with my Family. This Hotel was excellent, the breakfast was one of the best I've had in all my travels and the staff was great. The location was close to everything . Ill definitely recommend this Hotel
Reviewed on 30 May 2026
2 bedroom luxury Empire State VIEW
Manhattan
Save 100% on your flight
Price was AU$8,904, price is now AU$5,617 per person
AU$5,617
per person
14 Aug - 21 Aug
found 23 hours ago
Return direct flight included
Sydney (SYD) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on 19 Mar 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
Save 100% on your flight
Price was AU$6,019, price is now AU$3,857 per person
AU$3,857
per person
13 July - 20 July
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (3,526 reviews)
Great room and location
Reviewed on 29 May 2026
The Fifth Avenue Hotel
Manhattan
Save 100% on your flight
Price was AU$6,829, price is now AU$4,522 per person
AU$4,522
per person
14 Aug - 21 Aug
found 23 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.6/10 Exceptional! (222 reviews)
Room was beautiful, very European and chic. Carmenelli cafe is wonderful for breakfast and dinner, portrait is an extremely popular bar. Staff was very friendly.The view from our room was not very good.
Reviewed on 31 May 2026
Park Lane New York
Manhattan
Price was AU$4,288, price is now AU$2,869 per person
AU$2,869
per person
14 Aug - 21 Aug
found 23 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.4/10 Very Good! (1,784 reviews)
The room was exceptionally clean and very comfortable… the staff was especially awesome and helpful. Definitely we will stay there again.
Great location!
Thank you
Reviewed on 29 May 2026
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
61600 Main Rd Southold NY
The price is AU$549 per night from 11 June to 12 June
AU$549
11 June - 12 June
includes taxes & fees
9.4/10 Exceptional! (274 reviews)
"The room and balcony were both clean and spacious. No major complaints - just that blackout curtains don't exist on the larger windows, which can be an acquired taste for some. We went over Memorial Day weekend, which is typically the onset of beach season, and had wanted to use the beach passes ..."
Reviewed on 30 May 2026
Vine & Sand
47100 New York 25 Southold NY
The price is AU$683 per night from 4 June to 5 June
AU$683
4 June - 5 June
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 AU$141 per night from 7 June to 8 June
AU$141
7 June - 8 June
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"We used the place as a crash pad - easy to get to from the marina and close to "the main strip" . We did not have a car and it was a holiday weekend."
Reviewed on 28 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.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
AU$261
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.
