Southold Holidays
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Top Flight + Hotel Deals in Southold
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
Manhattan
Price was €2,475, price is now €1,527 per person
€1,527
per person
23 May - 30 May
found 14 hours ago
Return flight included
Athens (ATH) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,951 reviews)
The staff was extremely helpful in answering any questions we had and providing recommendations for restaurants and directions. The rooms and property were always clean. Breakfast provided many choices da and was always well stocked. The breakfast bone moves quickly and efficiently. The frosted glass shower/bathroom wall” was NOT an issue as the person in the bathroom could only be seen as a “blob.”
Reviewed on 14 Apr 2026
1 Hotel Brooklyn Bridge
Price was €3,187, price is now €1,887 per person
€1,887
per person
6 Jun - 9 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Don’t ever think you will check in prior to the late 4pm check in. No matter what. Not even 5 minutes.
Reviewed on 17 Apr 2026
1 Hotel Central Park
Manhattan
Save 100% on your flight
Price was €3,296, price is now €2,052 per person
€2,052
per person
1 Jun - 5 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,006 reviews)
Everything is great about this Hotel.
Reviewed on 9 Apr 2026
The Fifth Avenue Hotel
Manhattan
Price was €2,550, price is now €1,660 per person
€1,660
per person
6 Jun - 9 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (205 reviews)
I did not have breakfast, but I heard the breakfast. There is amazing. The bar was awesome. Great selection.!
Reviewed on 4 Apr 2026
Top hotels in Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is €186 per night from 30 Apr to 1 May
€186
30 Apr - 1 May
includes taxes & fees
9.4/10 Exceptional! (262 reviews)
The room was spacious. I’m very clean. I was very impressed. Location easy to get in and out of highly recommend.
Reviewed on 14 Apr 2026
Vine & Sand
47100 New York 25 Southold NY
The price is €350 per night from 20 Apr to 21 Apr
€350
20 Apr - 21 Apr
includes taxes & fees
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!
Reviewed on 22 Mar 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is €139 per night from 29 Apr to 30 Apr
€139
29 Apr - 30 Apr
includes taxes & fees
9.6/10 Exceptional! (465 reviews)
What a surprise?Amazing room, really well done on the renovation, beautiful property. Amenity bag with great snacks at check in.I was really surprised at this place, they know what they're doing
Reviewed on 18 Apr 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.
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.
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.
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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.
