Southold Holidays
Photo by Benny Goh
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Top Flight + Hotel Deals in Southold
Price found within the past 48 hours. Click for updated prices.
The Fifth Avenue Hotel
Manhattan
Save 100% on your flight
Price was €2,747, price is now €1,581 per person
€1,581
per person
19 Jan - 24 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (NYC)
9.6/10 Exceptional! (159 reviews)
What an incredibly beautiful place this hotel is! Staff cannot do enough and made ourspecial anniversary stay truly perfect..the hotel is beautifully decorated and immaculate throughout.
Cannot recommend this enough
Reviewed on 17 Nov 2025
1 Hotel Central Park
Manhattan
Save 100% on your flight
Price was €2,459, price is now €1,504 per person
€1,504
per person
19 Jan - 24 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (NYC)
9/10 Wonderful! (1,001 reviews)
Small hotel with small rooms, but the decor was very nice.
Reviewed on 28 Nov 2025
The Langham, New York, Fifth Avenue
Manhattan
Save 100% on your flight
Price was €2,434, price is now €1,600 per person
€1,600
per person
19 Jan - 24 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (1,001 reviews)
Clean spacious room. Courteous staff. Noise issue quickly resolved to our satisfaction.
Reviewed on 24 Nov 2025
Top hotels in Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is €183 per night from 1 Dec to 2 Dec
€183
1 Dec - 2 Dec
includes taxes & fees
9.4/10 Exceptional! (223 reviews)
My o
Reviewed on 24 Nov 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,002 reviews)
A well kept secret.
Reviewed on 26 Nov 2025
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is €174 per night from 30 Nov to 1 Dec
€174
30 Nov - 1 Dec
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Staff is fantastic
Reviewed on 24 Nov 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
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
€155
per adult
76% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
