Southold Holidays
Photo by Benny Goh
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Southold
Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Times Square
Manhattan
Save 100% on your flight
Price was €1,660, price is now €1,089 per person
€1,089
per person
23 Dec - 28 Dec
found 8 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,957 reviews)
La habitación un poco pequeña pero limpia lo único que el hotel es muy caro para lo que esperamos cuando llegamos y el elevador realmente da miedo porque suena mucho y va demasiado rápido piensas que te vas a cer de ahí en fuera no fue tal mal y estaba muy céntrico de todo
Reviewed on 13 Oct 2025
NobleDEN Hotel
Manhattan
Price was €2,678, price is now €1,616 per person
€1,616
per person
20 Nov - 24 Nov
found 9 hours ago
Return direct flight included
Warsaw (WAW) to New York (JFK)
9.8/10 Exceptional! (1,344 reviews)
This is my go to hotel! Do yourself a favor and get the balcony room!
Reviewed on 13 Oct 2025
Omni Berkshire Place
Manhattan
Save 100% on your flight
Price was €2,077, price is now €1,283 per person
€1,283
per person
23 Dec - 28 Dec
found 8 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (1,985 reviews)
The staff go out of their way to make you feel at home
Reviewed on 11 Oct 2025
Hotel 32 32
Manhattan
Save 100% on your flight
Price was €1,706, price is now €1,146 per person
€1,146
per person
23 Dec - 28 Dec
found 8 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8/10 Very Good! (2,177 reviews)
being in the room itself is very relaxing, could fix a few things maintenance wise but overall a great stay.
Reviewed on 14 Oct 2025
Top hotels in Southold
The Shoals Suites and Slips
61600 Main Rd, Southold, NY
The price is €260 per night from 15 Oct to 16 Oct
€260
15 Oct - 16 Oct
includes taxes & fees
9.4/10 Exceptional! (212 reviews)
"It was amazing"
Reviewed on 10 Oct 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is €79 per night from 15 Oct to 16 Oct
€79
15 Oct - 16 Oct
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Was clean and well maintained. Price was decent. Lack of breakfast was only minus."
Reviewed on 9 Oct 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is €93 per night from 2 Nov to 3 Nov
€93
2 Nov - 3 Nov
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Overall, a nice hotel for a one day trip! :)"
Reviewed on 5 Oct 2025
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.
Popular places to visit
Corey Creek Winery
You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
Horton Point Park
Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.
Mattebella Vineyards
You can enjoy a tasting or tour at Mattebella Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
What to do in Southold
Long Island Wine and Food Day Trip with Sommelier host from NYC
€126
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
€119
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
