Town of Southold Town Holidays

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Top Flight + Hotel Deals in Town of Southold Town

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

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was €3,235, price is now €2,235 per person
€2,235
per person
26 Dec - 1 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8.4/10 Very good! (1,813 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was €4,065, price is now €2,668 per person
€2,668
per person
26 Dec - 31 Dec
found 18 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The bar cafe in the lobby was amazing! Quick check in, clean property and very spacious rooms for this price point in NYC

Reviewed on 13 Nov 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was €4,005, price is now €2,635 per person
€2,635
per person
26 Dec - 31 Dec
found 1 day ago
Return flight included
Dublin (DUB) 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 €8,294, price is now €5,636 per person
€5,636
per person
26 Dec - 1 Jan
found 1 day ago
Return flight included
Dublin (DUB) 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

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was €3,343, price is now €2,351 per person
€2,351
per person
26 Dec - 31 Dec
found 22 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (1,536 reviews)
Some construction going on…it will be a truly fine hotel went completed.

Reviewed on 13 Nov 2026

Top hotels in Town of Southold Town

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is €180 per night from 14 Dec to 15 Dec
€180
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 €168 per night from 15 Nov to 16 Nov
€168
15 Nov - 16 Nov
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 €166 per night from 13 Dec to 14 Dec
€166
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.

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 €2,235. 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

€31
per adult
Mystic Seaport Museum Adventure
Paranormal Pub Crawl: Beer Tour

Paranormal Pub Crawl: Beer Tour

€67
per adult
Paranormal Pub Crawl: Beer Tour
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

€1,166
per traveller
The Hamptons and Long Island Wineries Private 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.