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.
OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,891, price is now €1,224 per person
€1,224
per person
2 May - 11 May
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Room was clean and staff was friendly.

Reviewed on 13 Feb 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €3,374, price is now €1,878 per person
€1,878
per person
2 May - 11 May
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
Nice hotel! Clean and spacious room.

Reviewed on 15 Feb 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Save 100% on your flight
Price was €2,496, price is now €1,647 per person
€1,647
per person
2 May - 11 May
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,000 reviews)
We had a great stay! Hospitality was spectacular, the room was very clean, and not to mention it’s very close to the 1681 Broadway Theatre. Highly recommend.

Reviewed on 15 Feb 2026

Park Central Hotel New York

Park Central Hotel New York

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,843, price is now €1,239 per person
€1,239
per person
2 May - 11 May
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
7.6/10 Good! (3,714 reviews)
The room was spotless comfortable , and met our needs.

Reviewed on 15 Feb 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 €167 per night from 17 Mar to 18 Mar
€167
17 Mar - 18 Mar
includes taxes & fees
8.4/10 Very Good! (610 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on 10 Jan 2026

Sound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is €144 per night from 17 Feb to 18 Feb
€144
17 Feb - 18 Feb
includes taxes & fees
8.8/10 Excellent! (566 reviews)
Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return!

Reviewed on 6 Feb 2026

The Harbor Front Inn
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is €163 per night from 16 Feb to 17 Feb
€163
16 Feb - 17 Feb
includes taxes & fees
9.4/10 Exceptional! (239 reviews)
Room was great. Clean and comfortable. Glad I found this place and will be back.

Reviewed on 22 Jan 2026

The Shoals Suites and Slips
See all 535 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 €1,224. 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.