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.
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was €1,291, price is now €899 per person
€899
per person
25 Jun - 29 Jun
found 16 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
8.6/10 Excellent! (1,923 reviews)
Well located and quiet.

Reviewed on 16 May 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was €2,081, price is now €1,267 per person
€1,267
per person
25 Jun - 29 Jun
found 16 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
9.2/10 Wonderful! (3,482 reviews)
Clean room and functional very convenient location from Midtown.

Reviewed on 17 May 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €2,453, price is now €1,549 per person
€1,549
per person
24 Jul - 31 Jul
found 3 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
9/10 Wonderful! (3,014 reviews)
The checking in process needs some updates

Reviewed on 16 May 2026

LENNOX HILL NYC

LENNOX HILL NYC

2 out of 5
Manhattan
Save 100% on your flight
Price was €2,924, price is now €2,020 per person
€2,020
per person
24 Jul - 31 Jul
found 3 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
No reviews
affordable. friendly online desk. seriously clean.

Reviewed on 7 May 2026

Ace Hotel New York

Ace Hotel New York

4 out of 5
Manhattan
Price was €1,731, price is now €1,206 per person
€1,206
per person
24 Jul - 31 Jul
found 3 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
8/10 Very Good! (1,098 reviews)
Great hotel and staff were great but the fact you had to pay for literally everything in the room was not well communicated and so charging for teabags and coffee was a bit of a shock.

Reviewed on 12 May 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 €334 per night from 19 May to 20 May
€334
19 May - 20 May
includes taxes & fees
8.4/10 Very Good! (647 reviews)
They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty.

Reviewed on 11 May 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 €326 per night from 18 May to 19 May
€326
18 May - 19 May
includes taxes & fees
8.8/10 Excellent! (598 reviews)
the rooms were clean. Staff as nice and helpful. i would stay again.

Reviewed on 16 May 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 €236 per night from 25 May to 26 May
€236
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (269 reviews)
Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend.

Reviewed on 5 May 2026

The Shoals Suites and Slips
See all 532 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 €899. 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.