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.
Sheraton New York Times Square Hotel
Manhattan
Save 100% on your flight
Price was €999, price is now €638 per person
€638
per person
26 Feb - 3 Mar
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7.4/10 Good! (5,413 reviews)
Everything was beautiful and excellent services.
Reviewed on 15 Jan 2026
Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was €2,417, price is now €1,303 per person
€1,303
per person
8 Apr - 14 Apr
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (2,790 reviews)
Everything was wonderful! Very comfortable and convenient!
Reviewed on 16 Jan 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
Save 100% on your flight
Price was €2,096, price is now €1,159 per person
€1,159
per person
8 Apr - 14 Apr
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
The beds are exceptionally comfortable and clean, and the breakfast offers delightful variety. The friendly staff ensures a welcoming atmosphere. I highly recommend Riu Plaza in Manhattan for a wonderful stay.
Reviewed on 13 Jan 2026
INNSiDE by Meliá New York Nomad
Manhattan
Price was €1,439, price is now €854 per person
€854
per person
18 Mar - 23 Mar
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
This hotel is a five star experience in every way. Highly recommended!
Reviewed on 16 Jan 2026
The Fifty Sonesta Hotel New York
Manhattan
Save 100% on your flight
Price was €1,774, price is now €1,094 per person
€1,094
per person
8 Apr - 14 Apr
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,302 reviews)
Great stay. Convenient location with many restaurants in the area.
Reviewed on 16 Jan 2026
Top hotels in Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is €166 per night from 21 Jan to 22 Jan
€166
21 Jan - 22 Jan
includes taxes & fees
9.4/10 Exceptional! (235 reviews)
Friendly staff, area was cleaned
Reviewed on 12 Jan 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is €241 per night from 21 Jan to 22 Jan
€241
21 Jan - 22 Jan
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Great room and staff
Reviewed on 14 Jan 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,000 reviews)
muy limpias
Reviewed on 8 Jan 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
