Southold Holidays from AU$2,404
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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.
NobleDEN Hotel
Manhattan
Save 100% on your flight
Price was AU$4,794, price is now AU$2,895 per person
AU$2,895
per person
14 Nov - 21 Nov
found 19 hours ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.8/10 Exceptional! (1,319 reviews)
My room was small but clean, quiet & comfortable. Hotel staff was very friendly & helpful. Location is close to loads of food options of all kinds & subway stops to get uptown or to Brooklyn easily.
Reviewed on 9 Sept 2025
W New York - Times Square
Manhattan
Save 100% on your flight
Price was AU$5,128, price is now AU$3,353 per person
AU$3,353
per person
20 Oct - 27 Oct
just found
Return direct flight included
Sydney (SYD) to New York (JFK)
8.6/10 Excellent! (1,807 reviews)
Everything was great. Just consider the mandatory destination fee.
Reviewed on 9 Sept 2025
The Michelangelo Hotel
Manhattan
Save 100% on your flight
Price was AU$4,629, price is now AU$3,125 per person
AU$3,125
per person
20 Oct - 27 Oct
just found
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,427 reviews)
About a five minute walk to Broadway and Times Square the staff was amazingly, friendly and helpful. The hotel itself was dated but in a good way.
Reviewed on 9 Sept 2025
Hotel 32 32
Manhattan
Price was AU$3,870, price is now AU$2,637 per person
AU$2,637
per person
20 Oct - 27 Oct
just found
Return direct flight included
Sydney (SYD) to New York (JFK)
8/10 Very Good! (2,155 reviews)
Sandra at the front desk was amazing however our room had black mold in the shower and wasn’t thoroughly cleaned.
Reviewed on 8 Sept 2025
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$611 per night from 28 Sept to 29 Sept
AU$611
28 Sept - 29 Sept
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 15 Sept to 16 Sept
AU$140
15 Sept - 16 Sept
includes taxes & fees
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
Long Island Wine and Food Day Trip with Sommelier host from NYC
AU$226
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
AU$213
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
