Southold Holidays from NZ$2,479
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Southold Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Candlewood Suites New York City-Times Square by IHG
Manhattan
Price was NZ$3,181, price is now NZ$2,479 per person
NZ$2,479
per person
6 May - 10 May
found 1 day ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,594 reviews)
Clean room, friendly staff, lots of nice little extras.
Reviewed on 13 Feb 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
Price was NZ$4,308, price is now NZ$2,995 per person
NZ$2,995
per person
6 May - 10 May
found 1 day ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
The room was spotless and offered an amazing view, conveniently located near everything.
Reviewed on 16 Feb 2026
Hyatt Grand Central New York
Manhattan
Price was NZ$4,336, price is now NZ$3,270 per person
NZ$3,270
per person
2 Apr - 8 Apr
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.2/10 Very Good! (6,333 reviews)
The hotel is practically central to everything in New York - it is next door to Grand Central station and still very quiet. Courteous staff, amazing foyer and brilliant setting. The room is spacious which is not known for hotels in New York and also.very clean but it needs a bit of TLC in my opinion.
Reviewed on 16 Feb 2026
OYO Times Square
Manhattan
Price was NZ$4,492, price is now NZ$3,505 per person
NZ$3,505
per person
2 Apr - 8 Apr
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Staff was very courteous. Room temperature was perfect and blackout curtains were great. Location excellent
Reviewed on 15 Feb 2026
Southold Holiday
Our pick of the best Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is NZ$295 per night from 18 Feb to 19 Feb
NZ$295
18 Feb - 19 Feb
includes taxes & fees
9.4/10 Exceptional! (239 reviews)
Room was great. Clean and comfortable. Glad I found this place and will be back.
Reviewed on 22 Jan 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is NZ$329 per night from 18 Mar to 19 Mar
NZ$329
18 Mar - 19 Mar
includes taxes & fees
8.4/10 Very Good! (610 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...
Reviewed on 10 Jan 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is NZ$401 per night from 24 Feb to 25 Feb
NZ$401
24 Feb - 25 Feb
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Great amenities, Beautiful view, and Caring Staff.
Reviewed on 12 Feb 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.
Discover the most popular places to visit in Southold
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
