Town of Southold Town Holidays from NZ$4,027

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Top destinations in Town of Southold Town

A fisherman's dinghy tied up at the shore in early autumn. Setauket Harbor, Long Island.
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Fishers Island

Fishers Island

The Latest Town of Southold Town Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Price was NZ$5,856, price is now NZ$4,027 per person
NZ$4,027
per person
17 Aug - 29 Aug
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.8/10 Excellent! (1,957 reviews)
a great stay! There was so much to do nearby. The room was clean, spacious, and comfortable. I would definitely stay here again.

Reviewed on 8 June 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was NZ$7,965, price is now NZ$5,162 per person
NZ$5,162
per person
17 Aug - 29 Aug
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (3,055 reviews)
It's a beautiful hotel and the breakfast that was included was the best I've ever had during a hotel stay. My view from the room was spectacular and very close to major attractions. Can't wait to stay there again.

Reviewed on 8 June 2026

Allegria Hotel

Allegria Hotel

4 out of 5
Price was NZ$7,803, price is now NZ$5,178 per person
NZ$5,178
per person
17 Aug - 29 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (1,318 reviews)
The staff was helpful and nice… was highly disappointed in the room the room was dusty the curtains were all ripped and no outlet on my side of the bed… The room was right across from elevation which made the room extremely noisy to be in

Reviewed on 9 June 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was NZ$6,204, price is now NZ$4,338 per person
NZ$4,338
per person
17 Aug - 29 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,398 reviews)
Great location and well maintained. Good size rooms, clean washrooms and comfortable beds.

Reviewed on 9 June 2026

Placemakr Wall Street

Placemakr Wall Street

4 out of 5
Manhattan
Price was NZ$6,300, price is now NZ$4,513 per person
NZ$4,513
per person
17 Aug - 29 Aug
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9.2/10 Wonderful! (923 reviews)
The location was still good for a Saturday stay with a lower rate b/c subway stations are close by as is Pier 11 to get over to DUMBO quickly. The neighborhood wasn’t a ghost-town even a good bit after midnight. Room was clean and nice.

Reviewed on 7 June 2026

Our pick of the best Town of Southold Town Hotel Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is NZ$875 per night from 30 June to 1 July
NZ$875
30 June - 1 July
includes taxes & fees
8.4/10 Very Good! (654 reviews)
"Great"

Reviewed on 1 June 2026

Sound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is NZ$319 per night from 10 June to 11 June
NZ$319
10 June - 11 June
includes taxes & fees
9.2/10 Wonderful! (317 reviews)
"We loved our stay at Zey Hotel. Perfect stay for us and our pup! James and the rest of the staff were so helpful anytime we had a question or special request. We’ll definitely be back to stay again."

Reviewed on 6 June 2026

Zey Hotel
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is NZ$672 per night from 16 June to 17 June
NZ$672
16 June - 17 June
includes taxes & fees
9.4/10 Exceptional! (279 reviews)
"I've stayed at this location many times, and I'll keep coming back, because it's possibly the most comfortable hotel I've ever stayed at, especially in the last fifteen years of having to rely on hotels for an overnight work schedule in the Hamptons."

Reviewed on 8 June 2026

The Shoals Suites and Slips
See all 521 properties in Town of Southold Town
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 Town of Southold Town holiday package cost?
Tailor make your Town of Southold Town holiday package from only NZ$4,027. Pick from any combination of flights, hotels and rental cars to put together the trip you've been dreaming about for ages. Don't forget to add on a few experiences or activities!
How do I get a cheap travel package to Town of Southold Town?
Bundling your hotel and flight with Expedia won't just save you time — it'll save you a nice amount too. A Town of Southold Town holiday package makes it a cinch to put together your dream adventure. With more than 550 airlines throughout the world to choose from, finding flights that fit your schedule won't be a challenge. Not only that, we have over 1 000 000 hotels globally to select from. Talk about choice! Whatever your budget, Expedia puts the world within your reach.
Where should I stay in Town of Southold Town?
With popular attractions such as 67 Steps Beach and Orient Point County Park in this area, look for a hotel located near either one. Macari Vineyards is another Town of Southold Town hot spot that pulls the crowds.
What are the top hotels in Town of Southold Town?
If you intend to stay in the Greenport West neighbourhood, some great options are The Harborfront Inn and Sound View Greenport. Pipes Cove is another well-known Town of Southold Town area. We recommend Zey Hotel or The Menhaden if you prefer this part of town.
How far in advance should I book my Town of Southold Town holiday?
It depends on the air carrier, but it's usually possible to browse through international flights on Expedia nearly a year in advance. While it's generally a good idea to book ahead of time, lucky customers will occasionally find a cheaper seat only weeks before their intended journey.
What does an Expedia Town of Southold Town travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your ideal Town of Southold Town holiday. You can also add on a few activities and tours once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll get discounts you won't find elsewhere.
What should I know before booking a Town of Southold Town travel package?
You'll land amazing savings when you combine your flights, hotels and rental cars into a travel package. Not just that, booking everything in one place simply makes planning easier. So why waste money or time? Whether you're organising an upscale romantic escape or a budget family adventure, have a look at our holiday packages today.
Can I choose my airline with a Town of Southold Town Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have access to more than 550 partner airlines throughout the world, so you have options galore when creating your Town of Southold Town escape.
If I'm not able to travel, can I cancel my Town of Southold Town holiday package?
We totally understand — life can throw you the odd curveball. If you've booked a Town of Southold Town holiday package and need to amend or cancel it, we can help. It's always worth checking out our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been longer than 24 hours, your airline, hotel or car rental company may charge a fee.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.