Southold Holidays from £951
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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.
The Chemists’ Club Hotel
Manhattan
Price was £2,537, price is now £1,090 per person
£1,090
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (425 reviews)
The staff was very welcoming and the room was very clean. It’s in a great location, and we’ll definitely be back.
Reviewed on 9 Jun 2026
Dream Midtown, by Hyatt
Manhattan
Price was £2,224, price is now £992 per person
£992
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,511 reviews)
Close to Central Park. Nice Staff. A restaurant on the first floor. My little efficiency room was perfect because I was not in it much. I could’ve used a hairdryer though. I will
Stay again !
Reviewed on 15 Jun 2026
Rockville Centre Hotel - JFK Airport
Price was £2,356, price is now £1,067 per person
£1,067
per person
21 Jul - 24 Jul
found 1 day ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,006 reviews)
It’s an older building but well maintained. The check in was fast and easy. Bed was comfortable. Bathroom clean. Breakfast was good. Shuttle service was great to and from JFK airport.
Reviewed on 13 Jun 2026
HGU New York
Manhattan
Price was £2,335, price is now £1,061 per person
£1,061
per person
22 Jul - 25 Jul
found 1 day ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,000 reviews)
GREAT PLACE!!! If you love staying at boutique hotels this is the place. Close to Herald Square in the middle of it all. So secluded and private you can walk right by it and not notice it. Then when you open the front door there's an incredible low key quite elegance that permeated through the property. Keep in mind its NOT the Waldorf nor the Ritz but its like a lovely cousin. There was a young man, don't recall his name, Nuyorican he said he is, he was AMAZZZZZZING!!! Great attitude and very professional. Kudos to him and the person that hired him. HIGHLY RECOMMEND for solo travelers, my room was small, but then again it had ALL I needed.
Reviewed on 18 Jun 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 £296 per night from 22 Jun to 23 Jun
£296
22 Jun - 23 Jun
includes taxes & fees
9.4/10 Exceptional! (283 reviews)
"If you are traveling to Southold, this is a very good choice. The property is nice and the staff extremely friendly. The room is satisfactory but I could not believe how strong it smelled of either air freshener or a febreeze type odor. I had a horrible headache the first night. Left windows and ..."
Reviewed on 17 Jun 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
The price is £228 per night from 23 Jun to 24 Jun
£228
23 Jun - 24 Jun
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"Everything was great, except that the pool was not ready.And the continental breakfast could have been much better"
Reviewed on 9 Jun 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is £86 per night from 16 Jul to 17 Jul
£86
16 Jul - 17 Jul
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"very nice stay"
Reviewed on 15 Jun 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
£140
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.
