Southold Holidays from NZ$3,342

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The Latest Southold Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was NZ$3,912, price is now NZ$3,342 per person
NZ$3,342
per person
2 Sept - 5 Sept
found 3 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
The location couldn't be better—right next to Times Square and just a short walk to the PABT. Given how central it is, the noise level is actually manageable. My room was quite spacious; honestly, you'd be hard-pressed to find a bigger room in Manhattan with this price. There's also a nice lounge area on the first floor with a TV, perfect for catching games. That said, a few things stood out as less than ideal: the Wi-Fi in my room was spotty at best, the king bed was oddly short for a king—I'm 5'10" and my feet actually hung off the end—and the motorized curtains had a mind of their own, occasionally opening and closing on their own. Even with those hiccups, I was really happy with my stay overall.

Reviewed on 3 July 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was NZ$4,693, price is now NZ$3,678 per person
NZ$3,678
per person
2 Sept - 5 Sept
found 3 hours ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,099 reviews)
Excellent location and really amazing breakfast buffet (better than expected)

Reviewed on 3 July 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was NZ$4,633, price is now NZ$3,648 per person
NZ$3,648
per person
2 Sept - 5 Sept
found 3 hours ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,632 reviews)
From check in to check out, was very efficient, breakfast was very good, large selection! Everyone was very helpful! Will stay here again!

Reviewed on 3 July 2026

Hilton Garden Inn New York/Manhattan-Midtown East

Hilton Garden Inn New York/Manhattan-Midtown East

3.5 out of 5
Manhattan
Price was NZ$4,037, price is now NZ$3,449 per person
NZ$3,449
per person
2 Sept - 5 Sept
found 3 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
7.8/10 Good! (1,737 reviews)
Very good

Reviewed on 30 June 2026

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was NZ$3,906, price is now NZ$3,397 per person
NZ$3,397
per person
2 Sept - 5 Sept
found 3 hours ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (2,240 reviews)
I had a great stay at this hotel. The check-in process was smooth, friendly, and fast, making for a welcoming start to my visit. The staff was helpful throughout my stay and always pleasant to interact with. My room was clean, comfortable, and well maintained. The hotel's midtown location was excellent, centrally located and convenient to everything I wanted to see and do. I would definitely stay here again and recommend it to anyone looking for a comfortable, well-located hotel with great service.

Reviewed on 2 July 2026

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 NZ$790 per night from 27 July to 28 July
NZ$790
27 July - 28 July
includes taxes & fees
9.4/10 Exceptional! (291 reviews)
"Incredibly beautiful place and perfectly clean!"

Reviewed on 26 June 2026

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 NZ$180 per night from 9 July to 10 July
NZ$180
9 July - 10 July
includes taxes & fees
8/10 Very good! (1,002 reviews)
"staff and parking"

Reviewed on 22 June 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 NZ$1,098 per night from 7 July to 8 July
NZ$1,098
7 July - 8 July
includes taxes & fees
8.4/10 Very good! (661 reviews)
"Amazing views Rooms were just right People were pleasant BEach chairs and towels readily available Otherwise had a great time Service at the restaurant very slow"

Reviewed on 2 July 2026

Sound View Greenport
See all 4,382 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.

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

NZ$322
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 NZ$3,342 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.