Southold Holidays from AU$3,305

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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.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
27 Aug - 3 Sept
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
8.8/10 Excellent! (1,653 reviews)
Love this place! Great service and room was amazing!

Reviewed on 25 Jul. 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
27 Aug - 3 Sept
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
9.8/10 Exceptional! (1,232 reviews)
Everything you need for your stay in NYC. We really enjoyed our stay. The hotel is clean and the rooms have good space. The staff was really nice with us and our 2 year old baby. The location is perfect because there are lots of options of shops and restaurants around. We will definitely go back to this hotel on our next trip to NY.

Reviewed on 25 Jul. 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (2,098 reviews)
I had never heard of this hotel before our stay, but we arrived and it did not disappoint! We visited during a busy time so early check in was not available, but they did their best to accommodate us. They were able to hold our luggage while we explored until our room was ready. My favorite thing was definitely that this hotel is in the center of everything! The restaurant downstairs was great, also.

Reviewed on 25 Jul. 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
per person
16 Oct - 21 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to New York (JFK)
9.2/10 Wonderful! (3,370 reviews)
Great location and good size clean room

Reviewed on 25 Jul. 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
16 Oct - 21 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to New York (JFK)
9/10 Wonderful! (2,714 reviews)
Ideal location for exploring New York. Breakfast buffet was excellent.

Reviewed on 23 Jul. 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$666 per night from 17 Aug to 18 Aug
AU$666
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (185 reviews)
"The room was beautiful and clean. Very easy to get around and go into town. There was a restaurant walking distance. Everything else is a short car ride or uber ride away. Everyone was extremely friendly and willing to help out when needed. I would definitely recommend!"

Reviewed on 20 Jul. 2025

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25, Southold, NY
10/10 Exceptional! (7 reviews)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport."

Reviewed on 17 Feb. 2025

Get rates
Vine & Sand
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 31 July to 1 Aug
AU$191
31 July - 1 Aug
includes taxes & fees
7.6/10 Good! (1,009 reviews)
"The room was clean, bed and pillows comfortable. A/C worked well. Plenty of on site parking"

Reviewed on 23 Jul. 2025

Quality Inn Old Saybrook - Westbrook
See all 4,423 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$243
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$210
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$3,305 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.