Town of Southold Town Holidays from AU$2,553

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Town of Southold Town

A pebble beach at sunset with a calm sea in the background.
FlightsFlightsHotelsHotels

Mattituck

Mattituck

The Latest Town of Southold Town Holiday Deals

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

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was AU$3,742, price is now AU$2,553 per person
AU$2,553
per person
21 Jan - 30 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was AU$12,051, price is now AU$6,304 per person
AU$6,304
per person
18 Jan - 27 Jan
found 23 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on 6 Nov 2026

LGA AIRPORT

LGA AIRPORT

2 out of 5
Queens
Price was AU$11,058, price is now AU$7,369 per person
AU$7,369
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
10/10 Exceptional! (2 reviews)
The best airbnb Ive stayed at in New York with the best price for our family of 6. The place was so clean, amenities looked brand new. It had a homey feel to it, my kids didnt want to leave. We will definently be booking again in the future.

Reviewed on 24 Dec 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was AU$3,893, price is now AU$2,622 per person
AU$2,622
per person
21 Jan - 30 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
I appreciate the need to conserve electricity, but the key card in the slot unfortunately meant we were coming back to a warm room.

Reviewed on 13 Nov 2026

The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Price was AU$10,450, price is now AU$7,324 per person
AU$7,324
per person
22 Dec - 3 Jan
found 6 hours ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.4/10 Exceptional! (275 reviews)

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

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is AU$290 per night from 14 Dec to 15 Dec
AU$290
14 Dec - 15 Dec
includes taxes & fees
Sound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is AU$261 per night from 14 Dec to 15 Dec
AU$261
14 Dec - 15 Dec
includes taxes & fees
Zey Hotel
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is AU$254 per night from 13 Dec to 14 Dec
AU$254
13 Dec - 14 Dec
includes taxes & fees
9/10 Wonderful! (676 reviews)
"Clean and comfortable room. Great location to walk around town. Nice continental breakfast."

Reviewed on 11 Nov 2026

The Harbor Front Inn
See all 506 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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$2,553. 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.

Stay near popular Town of Southold Town attractions

Sunflowers in a field with a building in the background.
Photo by 4 Star Traveler
Open Photo by 4 Star Traveler

Pindar Vineyards

8.4/10 (8 reviews)
You can enjoy a tasting or tour at Pindar Vineyards during your travels to Peconic. Discover the area's sunsets and wineries.
See properties

What to do in Town of Southold Town

Mystic Seaport Museum Adventure

Mystic Seaport Museum Adventure

AU$50
per adult
92% of travellers recommend
Mystic Seaport Museum Adventure
Downtown Westerly Ghost Tour

Downtown Westerly Ghost Tour

AU$50
per adult
100% of travellers recommend
Downtown Westerly Ghost Tour
Paranormal Pub Crawl: Beer Tour

Paranormal Pub Crawl: Beer Tour

AU$107
per adult
Paranormal Pub Crawl: Beer Tour
See all activities in Town of Southold Town
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.