Southold Holidays from AU$3,186

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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.
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was AU$4,310, price is now AU$3,186 per person
AU$3,186
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (4,331 reviews)
Hotel location is good - staff helpful The real issue we faced id they charge a resort fee which most hotels do However on several days the pool area and rooftop bar were closed to the public for private events No advance warning given and no compensation

Reviewed on 17 July 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$5,332, price is now AU$3,530 per person
AU$3,530
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (3,130 reviews)

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Price was AU$4,609, price is now AU$3,346 per person
AU$3,346
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.4/10 Very good! (1,007 reviews)
Breakfast left a lot to be desired but other

Reviewed on 18 July 2026

Library Hotel by Library Hotel Collection

Library Hotel by Library Hotel Collection

4 out of 5
Manhattan
Price was AU$4,857, price is now AU$3,573 per person
AU$3,573
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9.6/10 Exceptional! (1,004 reviews)
O hotel tem localização privilegiada, funcionários prestativos e educados.

Reviewed on 14 July 2026

The Iroquois New York

The Iroquois New York

4.5 out of 5
Manhattan
Price was AU$5,179, price is now AU$3,944 per person
AU$3,944
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9.4/10 Exceptional! (1,760 reviews)
GREAT location & staff! Loved the room & view of Chrysler Building! Excellent dining as well! Close to everything and subways! Will definitely stay here again!

Reviewed on 17 July 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

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is AU$643 per night from 26 July to 27 July
AU$643
26 July - 27 July
includes taxes & fees
The Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is AU$151 per night from 19 July to 20 July
AU$151
19 July - 20 July
includes taxes & fees
8/10 Very good! (1,002 reviews)
"The staff was delightful!!! We stayed for a week and it was in a good location with lots of restaurants and the beach is very close."

Reviewed on 17 July 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is AU$776 per night from 9 Aug to 10 Aug
AU$776
9 Aug - 10 Aug
includes taxes & fees
Sound View Greenport
See all 4,371 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
Sparkling Pointe crafts exquisite sparkling wines using traditional Méthode Champenoise in their Southold vineyard. Savour their diverse bubblies in an elegant tasting room with vineyard views.
See properties

What to do in Southold

great fun with friends

Full Day Private Long Island Wine Tours from New York City

AU$273
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Southold

Frequently asked questions

How much does a Southold holiday package cost?
You can snap up a holiday package to this top destination from AU$3,186 on Expedia. However, how much your holiday to Southold costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Southold?
January, February and March are great times to look for cheap Southold holiday packages. Choosing to travel in quieter months means you can generally find better prices on flights and hotels.
How many days is enough for Southold?
Dedicate at least 3 days for your Southold holiday to immerse yourself in everything that makes this place unique. Explore popular areas, including Greenport West and Pipes Cove. Then head to the major sights like Osprey's Dominion and Croteaux Vineyards. With a good itinerary, you can keep busy with room for some me-time too. Want to travel beyond Southold? Consider an excursion or two.
How to find the best Southold package deals?
Bagging a cheap Southold package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Southold package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Southold holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalise your Southold escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Southold?
If you're planning a spur-of-the-moment Southold holiday, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Southold?

  1. Choose your dates: The things you'd like to do in Southold and your favourite season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodation will likely be the largest expense during your trip to Southold.
  3. Decide how long to go for: Now that you know more about Southold, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customised Southold holiday package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.