Town of Southold Town Holidays

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    Save up to €185 when you book a flight and hotel together*

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Top Flight + Hotel Deals in Town of Southold Town

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was €974, price is now €610 per person
€610
per person
28 Jan - 1 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (NYC)
18.4/10 Exceptional! (2,007 reviews)
Great room and polite staff and excellent restaurant and location.

Reviewed on 15 Nov 2025

Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,181, price is now €665 per person
€665
per person
8 Jan - 13 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (NYC)
16.4/10 Exceptional! (1,943 reviews)
Rooms left much to be desired. Not a proper placement to room anyone considering rooms were being renovated above which directly affected the plumbing in our room.

Reviewed on 27 Oct 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was €2,493, price is now €1,404 per person
€1,404
per person
8 Jan - 13 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (NYC)
17.6/10 Exceptional! (1,003 reviews)
Overall, we loved everything about 1 hotel Brooklyn Bridge. It was a birthday gift trip for my husband, and he enjoyed every minute of our stay. Thank you and we will be back again! Definitely a 5 star hotel and will recommend to my friends.

Reviewed on 9 Nov 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was €4,458, price is now €2,582 per person
€2,582
per person
22 Dec - 28 Dec
found 1 day ago
Return direct flight included
Amsterdam (AMS) to New York (NYC)
19.2/10 Exceptional! (158 reviews)
Nice and well centered

Reviewed on 15 Nov 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was €2,161, price is now €1,322 per person
€1,322
per person
8 Jan - 13 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (NYC)
18/10 Exceptional! (1,003 reviews)
Nice looking hotel, but the walls are paper thin and you can hear everything from the other rooms. Would not recommend.

Reviewed on 16 Nov 2025

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 €233 per night from 17 Dec to 18 Dec
€233
17 Dec - 18 Dec
includes taxes & fees
8.4/10 Very Good! (590 reviews)
Beautiful and unique property. We really enjoyed our weekend getaway

Reviewed on 13 Nov 2025

Sound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
The price is €175 per night from 17 Dec to 18 Dec
€175
17 Dec - 18 Dec
includes taxes & fees
8.6/10 Excellent! (533 reviews)
Very nice person on the desk and happy to greet me as a late arrival.

Reviewed on 13 Nov 2025

The Harbor Front Inn
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street, Greenport, NY
9/10 Wonderful! (287 reviews)
Spotless room, wonderfully comfortable bed, beautiful decorating job and the sweetest, nicest front desk person - Jessica, who made us feel welcome!

Reviewed on 11 Nov 2025

Get rates
Zey Hotel
See all 550 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 €610. 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.