
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.

Hotel Riu Plaza Manhattan Times Square
Manhattan
Price was €1,513, price is now €919 per person
€919
per person
31 Oct - 3 Nov
found 11 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,368 reviews)
One block from Times Square busy yet so centrally located to all we wanted to see!
We enjoyed the hotel and we could walk or use the subway system just on the corner. Many nearby restaurants and stores. Great service and clean rooms! Wifi is an additional charge.
Reviewed on 18 Aug 2025

Hotel 32 32
Manhattan
Save 100% on your flight
Price was €1,772, price is now €950 per person
€950
per person
7 Oct - 13 Oct
found 1 day ago
Return flight included
Toronto (YYZ) to New York (JFK)
8/10 Very Good! (2,135 reviews)
I really enjoyed the hotel. It was perfect for me and my partner. It was just the two of us. I did search a lot for a hotel with a balcony and I finally found this one. I will definitely recommend it. I will definitely come back again.
Reviewed on 19 Aug 2025



Pestana Park Avenue
Manhattan
Save 100% on your flight
Price was €2,095, price is now €1,242 per person
€1,242
per person
30 Oct - 5 Nov
found 1 hour ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (688 reviews)
The front desk staff were very friendly, the room was clean and spacious.
Reviewed on 15 Aug 2025
Top hotels in Southold

The Shoals Suites and Slips
61600 Main Rd, Southold, NY
The price is €385 per night from 26 Aug to 27 Aug
€385
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (192 reviews)
"The hotel was lovely"
Reviewed on 9 Aug 2025

Vine & Sand
47100 New York 25, Southold, NY
10/10 Exceptional! (9 reviews)
"Beautiful house and trip to stay in the North Fork. Hosts are incredible. Highly recommend!!"
Reviewed on 23 Jul 2025

Greenview Inn Riverhead
1433 W Main St, Riverhead, NY
Fully refundableReserve now, pay when you stay
7.2/10 Good! (699 reviews)
"Nice"
Reviewed on 18 Aug 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
€128
per adult

From Mattituck: North Fork Area Bike Tour with Food Tasting
€120
per adult
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.