Town of Southold Town Holidays

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    Better together
    Save up to €185 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Town of Southold Town

Price found within the past 48 hours. Click for updated prices.
The Manhattan at Times Square

The Manhattan at Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
7 Aug - 14 Aug
found 23 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
5.8/10 (4,356 reviews)
Very nice hotel and convenient to Yankees stadium and Times Square. Very happy!

Reviewed on 28 Jun 2025

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
per person
7 Aug - 14 Aug
found 23 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
9.6/10 Exceptional! (1,003 reviews)
nice place to stay staff is nice

Reviewed on 27 Jun 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
per person
4 Sept - 9 Sept
found 7 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8/10 Very Good! (2,051 reviews)
Good location, large room. The big draw back is water leaking from the ceiling.

Reviewed on 25 Jun 2025

The Gardens Sonesta ES Suites New York

The Gardens Sonesta ES Suites New York

3 out of 5
Manhattan
Save 100% on your flight
per person
7 Aug - 14 Aug
found 23 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Rooms can smell funny like smoke

Reviewed on 25 Jun 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
5 Sept - 11 Sept
found 12 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
It was nice but certainly not extraordinary. It was also outlandishly expensive. However the staff was outstanding.

Reviewed on 24 Jun 2025

Top hotels in Town of Southold Town

Greenporter Hotel
Greenporter Hotel
2 out of 5
326 Front St, Greenport, NY
9.2/10 Wonderful! (120 reviews)
"We love this hotel"

Reviewed on 23 Jun 2025

Get rates
Greenporter Hotel
Sound View Greenport
Sound View Greenport
4 out of 5
58775 County Rd 48, Greenport, NY
The price is €457 per night from 30 Jul to 31 Jul
€457
30 Jul - 31 Jul
includes taxes & fees
8.4/10 Very Good! (531 reviews)
"We had an overall great stay and will be back. Especially loved nights out on the beach!"

Reviewed on 22 Jun 2025

Sound View Greenport
Silver Sands Motel & Beach Bungalows
Silver Sands Motel & Beach Bungalows
4 out of 5
1400 Silvermere Rd, Greenport, NY
9.6/10 Exceptional! (98 reviews)
"This property is a treasure. Think Palm Springs meets Adirondacks. If you are overworked and stressed out this is an ideal spot for relaxing in the summer. Food is exceptionally good. Lounging under the umbrella beach side combined with a refreshing swim makes your dreams come true. Staff members ..."

Reviewed on 25 Jun 2025

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Silver Sands Motel & Beach Bungalows
See all 572 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 €845. 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.