Southold Holidays from £1,580
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Your Southold Holiday
The coastal scenery and rich history are just the beginning of the things Southold has going for it. Experience the very best of this interesting city your way with a customised Southold holiday package. 67 Steps Beach, Raphael Winery and Railroad Museum of Long Island are just some of the many sights worth checking out during your trip to Southold. A few quick clicks is all it takes to put together your ideal Southold holiday on Expedia.
Top Southold Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Placemakr Wall Street
Manhattan
Save 100% on your flight
Price was £2,451, price is now £1,580 per person
£1,580
per person
23 Jun - 30 Jun
found 1 day ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (910 reviews)
The place was quite, staff was friendly. Clean and cozy rooms.
Reviewed on 6 Apr 2026
2 bedroom luxury Empire State VIEW
Manhattan
Price was £4,332, price is now £1,789 per person
£1,789
per person
8 Jul - 12 Jul
found 23 hours ago
Return direct flight included
London (LHR) to New York (JFK)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on 19 Mar 2026
1 Hotel Brooklyn Bridge
Save 100% on your flight
Price was £3,389, price is now £1,896 per person
£1,896
per person
8 Jul - 12 Jul
found 23 hours ago
Return direct flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,005 reviews)
Stayed at 1 Hotel Brooklyn Bridge for our 5 year wedding anniversary and had an amazing experience. The staff was friendly, welcoming, and super helpful throughout our stay. Loved the relaxed vibe and casual style from the staff because it made the hotel feel comfortable instead of overly formal. The rooftop bar was next level with incredible views of the river and the Brooklyn Bridge. Very happy with our stay overall and would definitely come back.
Reviewed on 2 May 2026
5th & 55th Residence Club
Manhattan
Save 100% on your flight
Price was £3,921, price is now £2,514 per person
£2,514
per person
8 Jul - 12 Jul
found 23 hours ago
Return direct flight included
London (LHR) to New York (JFK)
8.4/10 Very Good! (5 reviews)
We loved this hotel. The room was beautiful and very comfortable. Excellent lighting for reading. Bathroom was great with unbelievable water pressure in both bath and shower. Wonderful cleaning staff. Great trip.
Reviewed on 13 Feb 2023
Loews Regency New York Hotel
Manhattan
Save 100% on your flight
Price was £2,496, price is now £1,632 per person
£1,632
per person
25 Jun - 29 Jun
found 16 hours ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Just wonderful
The staff at the hotel are magnificent
Alway consistent always fantastic
We will return time and time again!
Concierge are the best in the city…
Reviewed on 28 Apr 2026
Southold Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Population | 5,700 |
Max Temp Winter | 4ºC |
Max Temp Summer | 24ºC |
Top Sights | 67 Steps Beach, Macari Vineyards and Kontokosta Winery |
Top hotels in Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is £202 per night from 11 May to 12 May
£202
11 May - 12 May
includes taxes & fees
9.4/10 Exceptional! (266 reviews)
My girlfriend and I stayed in April and it was amazing stay. Rooms are outstanding, one of the best rooms we ever stayed, and location was stunning. Beautiful marina, great waterfront views from the property. It was so quiet and relaxing. We went to Greenport for dinners. 10$ Breakfast cards were ...
Reviewed on 25 Apr 2026
Vine & Sand
47100 New York 25 Southold NY
The price is £274 per night from 10 May to 11 May
£274
10 May - 11 May
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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is £67 per night from 11 May to 12 May
£67
11 May - 12 May
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Parking was easy. Bed mattress terrible. Tired room and furnishings. Basic supplies.
Reviewed on 28 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.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
£139
per adult
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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. Flight-inclusive packages are ATOL protected.
