Town of Southold Town Holidays from AU$2,860

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Top destinations in Town of Southold Town

FlightsFlightsHotelsHotels

Mattituck

Mattituck

The Latest Town of Southold Town Holiday Deals

Price found within the past 48 hours. Click for updated prices.
OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was AU$3,991, price is now AU$2,860 per person
AU$2,860
per person
19 Mar - 28 Mar
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Amazing staff!! Room was chilly despite the heat being on and high, better windows definitely needed, other than this, no complaints!

Reviewed on 30 Dec 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was AU$4,911, price is now AU$3,272 per person
AU$3,272
per person
19 Mar - 28 Mar
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Happy to have stayed there. Overall good experience

Reviewed on 31 Dec 2025

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was AU$4,212, price is now AU$2,910 per person
AU$2,910
per person
19 Mar - 28 Mar
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
7.4/10 Good! (5,413 reviews)
In general, the service was very good; however, we had to wait seven hours to get a room because it was not ready yet. I understand that the staff may have been understaffed due to the busy season. I would like to stay at this hotel again and hope that I won’t face the same situation next time.

Reviewed on 31 Dec 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was AU$4,253, price is now AU$3,001 per person
AU$3,001
per person
19 Mar - 28 Mar
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
The room was incredibly warm, we were unable to adjust the temperature in our room and it was recommended we open the window. There was no window screen and we had a stairs leading up to our room from our window.

Reviewed on 31 Dec 2025

Hotel 57

Hotel 57

4 out of 5
Manhattan
Price was AU$3,984, price is now AU$2,959 per person
AU$2,959
per person
19 Mar - 28 Mar
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.2/10 Very Good! (1,287 reviews)
On your web site you stated there was a restaurant in Hotel 57: one year ago that was closed. For Breakfast there was just a McDonald’s next door. Several coffee shops but without seating on their premises. Rooms very small & no room for a comfortable chair in room. Room clean & good bathroom. Excellent location for East side of NYC.

Reviewed on 29 Dec 2025

Town of Southold Town Essential Information

Language
English
Currency
U.S dollars
Closest Airport
MacArthur Airport (ISP)
Top Sights
67 Steps Beach, Harbes Family Farm and Orient Point County Park

Our pick of the best Town of Southold Town Hotel Deals

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is AU$273 per night from 1 Feb to 2 Feb
AU$273
1 Feb - 2 Feb
includes taxes & fees
8.8/10 Excellent! (552 reviews)
Great check in experience. Very nice room

Reviewed on 27 Dec 2025

The Harbor Front Inn
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is AU$312 per night from 28 Jan to 29 Jan
AU$312
28 Jan - 29 Jan
includes taxes & fees
8.4/10 Very Good! (601 reviews)
Great room with amazing views! Staff was fantastic and the food was great too

Reviewed on 28 Nov 2025

Sound View Greenport
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is AU$278 per night from 8 Jan to 9 Jan
AU$278
8 Jan - 9 Jan
includes taxes & fees
9.4/10 Exceptional! (231 reviews)
Overall excellent experience during the off-season at this new seaside hotel…Large rooms with separate kitchen/living room areas, modern and elegant, friendly check-in service, and expansive lobby area with lots of seating and spectacular water views.

Reviewed on 23 Dec 2025

The Shoals Suites and Slips
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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.
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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 AU$2,860. 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.