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.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was €1,654, price is now €894 per person
€894
per person
6 Feb - 14 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Excellent Stay. Exceptionally clean. I would highly recommend as very central for all New York attractions and I would stay here again

Reviewed on 1 Jan 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was €3,827, price is now €2,006 per person
€2,006
per person
13 Mar - 20 Mar
found 7 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
V nice location and staff

Reviewed on 1 Jan 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was €2,789, price is now €1,520 per person
€1,520
per person
13 Mar - 20 Mar
found 7 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Had a wonderful visit!

Reviewed on 28 Dec 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was €3,396, price is now €1,932 per person
€1,932
per person
13 Mar - 20 Mar
found 7 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
The Hotel is in a great location, just minutes from great shopping, restaurants, and of course Central Park. What really made me give 5 stars is the Shane at the front. He makes you feel so welcomed and always goes above and beyond to make sure you're having a great stay.

Reviewed on 29 Dec 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was €4,214, price is now €2,506 per person
€2,506
per person
13 Mar - 20 Mar
found 7 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (159 reviews)
Very enjoyable place. Loved the size and rooms were smartly efficient but felt special. Excellent staff

Reviewed on 31 Dec 2025

Top hotels in Town of Southold Town

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is €156 per night from 1 Feb to 2 Feb
€156
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 €163 per night from 14 Jan to 15 Jan
€163
14 Jan - 15 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 €180 per night from 7 Jan to 8 Jan
€180
7 Jan - 8 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
See all 540 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 €894. 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.