Southold Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$134 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
Top hotels in Southold
The Shoals Suites and Slips
Clean, spacious and thoughtful room amenities. Close by to town and great restaurants.
Reviewed on 23 Mar, 2026
Vine & Sand
Location was perfect for visiting the wineries… breakfast was to die for!
Reviewed on 22 Mar, 2026
Water's Edge Resort & Spa
Very pleasurable experience here. It’s not something we’ll do every year, as it is expensive. Spa services are especially expensive. Nonetheless, the staf performed flawlessly. Food was excellent. Grounds were well cared for.
Reviewed on 23 Mar, 2026
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
Full Day Private Long Island Wine Tours from New York City
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. 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.
