Southold Holidays from AU$4,442

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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.
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Manhattan
per person
10 May - 16 May
found 1 day ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.2/10 Wonderful! (707 reviews)
Absolutely the best hotel I’ve ever stayed in. First time in NY, and 33 Hotel is in the perfect location for balancing time between Brooklyn & Manhattan.

Reviewed on 30 Mar. 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
10 May - 16 May
found 1 day ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
My wife and I had a wonderful time staying here. Definitely recommend for the couple trying to use their hotel as an luxurious oasis from the city that never sleeps.

Reviewed on 25 Mar. 2025

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
per person
30 Apr - 6 May
found 21 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.8/10 Excellent! (1,007 reviews)
Great location and value for money!

Reviewed on 23 Mar. 2025

The Ritz-Carlton New York, Central Park

The Ritz-Carlton New York, Central Park

5 out of 5
Manhattan
per person
10 May - 16 May
found 1 day ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.2/10 Wonderful! (471 reviews)
Wonderful and clean property, and very kind staff. It was a very enjoyable stay.

Reviewed on 26 Dec. 2024

Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Manhattan
per person
10 May - 16 May
found 1 day ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.8/10 Exceptional! (406 reviews)
Very lovely and responsive staff

Reviewed on 28 Mar. 2025

Southold Holiday

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$347 per night from 13 Apr to 14 Apr
AU$347
includes taxes & fees
13 Apr - 14 Apr
9.4/10 Exceptional! (154 reviews)
"great location and view"

Reviewed on 19 Mar. 2025

The Shoals Suites and Slips
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$370 per night from 2 Apr to 3 Apr
AU$370
includes taxes & fees
2 Apr - 3 Apr
8.6/10 Excellent! (1,001 reviews)
Excellent stay
"It was a lovely one night stay with a friend. The room was beautiful, the hotel was stunning, and the check in was great. Lots of recommendations for good places to go. Very pleasant experience!"

Reviewed on 26 Mar. 2025

Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 31 Mar to 1 Apr
AU$126
includes taxes & fees
31 Mar - 1 Apr
7.6/10 Good! (933 reviews)
"Great rates, easy check in, convenient location. Room is small and cozy, and clean. Bathroom leaves much to be desired"

Reviewed on 27 Mar. 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,272 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.

Frequently asked questions

How much does a Southold holiday package cost?
You can snap up a holiday package to this top destination from AU$4,442 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.