Southold Holidays from AU$3,132

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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.
Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
7.8/10 Good! (1,511 reviews)
I liked the room and hotel, looked nice clean. Didn't like, towels were rationed a bit too much and access to the pool. The staff wasn't very helpful to accommodate seating.

Reviewed on 12 Aug. 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
17 Oct - 24 Oct
found 22 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (3,368 reviews)
A hotel with an excellent location in the center of NY. Clean, quiet room, air conditioning, safe and refrigerator. Excellent breakfast. No slippers or toiletries (razor, toothbrush, etc.).

Reviewed on 13 Aug. 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
17 Oct - 24 Oct
found 22 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (2,737 reviews)
Very nice property close to theaters and Times Square. Relatively easy to get to, but be sure you don’t have your cab or Uber take you to the other Riu hotel in the area like we did. Not a long walk but different location

Reviewed on 10 Aug. 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (2,085 reviews)
all around great city hotel. good restuarant, clean, modern rooms, nice amenities. great service.

Reviewed on 12 Aug. 2025

The Knickerbocker Hotel

The Knickerbocker Hotel

5 out of 5
Manhattan
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,569 reviews)
From the first person who checked us in (Lucy) to Jay, the concierge to Andre, one of the excellent bellman our stay was perfect. Will never stay at another place in New York. Rooms were great, rooftop bar was beautiful and had great cocktails. Great location especially if you are theatre people. Walked everywhere easily! 5+stars

Reviewed on 12 Aug. 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

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is AU$689 per night from 14 Aug to 15 Aug
AU$689
14 Aug - 15 Aug
includes taxes & fees
9.4/10 Exceptional! (191 reviews)
"The hotel was lovely"

Reviewed on 9 Aug. 2025

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25, Southold, NY
10/10 Exceptional! (9 reviews)
"Beautiful house and trip to stay in the North Fork. Hosts are incredible. Highly recommend!!"

Reviewed on 23 Jul. 2025

Get rates
Vine & Sand
Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St, Riverhead, NY
Fully refundableReserve now, pay when you stay
7.2/10 Good! (678 reviews)
"ROOMS ARE VERY COZY !"

Reviewed on 7 Aug. 2025

Get rates
Greenview Inn Riverhead
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

What to do in Southold

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

AU$227
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

AU$212
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
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$3,132 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.

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