Southold Holidays
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- Better togetherSave up to S$134 when you book a flight and hotel together*
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Top hotels in Southold
The Shoals Suites and Slips
Everything was Amazing!
Reviewed on 28 Oct, 2025
Pier Blue Inn Old Saybrook - Essex
The room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...
Reviewed on 3 Nov, 2025
Quality Inn Old Saybrook - Westbrook
It was a nice clean hotel.
Reviewed on 27 Oct, 2025
Popular places to visit
Croteaux Vineyards
You can enjoy a tasting or tour at Croteaux Vineyards 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.
What to do in Southold
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
Half-Day Private Long Island Wine Tour Experience
Long Island Wine Tour North Fork Sights Bites Flights Half Day AM
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
