Southold Holidays from NZ$21,009

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The Latest Southold Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
per person
10 Sept - 15 Sept
found 3 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.2/10 Wonderful! (3,397 reviews)
everything is perfect, bed is comfortable, everything is clean. Excellent!

Reviewed on 23 Jun. 2025

Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Manhattan
per person
10 Sept - 15 Sept
found 3 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.8/10 Exceptional! (424 reviews)
What a great week I had in New York. I’ll definitely be back. Oksana and Daniel were amazing.

Reviewed on 28 May 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
per person
10 Sept - 15 Sept
found 3 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
Great job keeping up with the technology. We liked that.

Reviewed on 24 Jun. 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
10 Sept - 15 Sept
found 3 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (2,727 reviews)
The room was very clean, apart from dust build up, under the bed.

Reviewed on 23 Jun. 2025

The Dominick

The Dominick

5 out of 5
Manhattan
per person
10 Sept - 15 Sept
found 3 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
There is a restaurant in the same building Aitana that is spectacular, I recommend it.

Reviewed on 20 Jun. 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
9.4/10 Exceptional! (173 reviews)
"Amazing"

Reviewed on 15 Jun. 2025

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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

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Vine & Sand
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
The price is NZ$167 per night from 29 June to 30 June
NZ$167
29 June - 30 June
includes taxes & fees
7.6/10 Good! (979 reviews)
"Property was clean buy outdated."

Reviewed on 23 Jun. 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,395 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 NZ$21,009 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.

Discover the most popular places to visit in Southold

Mattebella Vineyards

You can enjoy a tasting or tour at Mattebella Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Mattebella Vineyards

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

NZ$264
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
See all activities in Southold
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.