Southold Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is 4.413.052 ₫ per night from 2 Mar to 3 Mar
4.413.052 ₫
5.041.912 ₫ total
2 Mar - 3 Mar
includes taxes & fees
9.4/10 Exceptional! (242 reviews)
Clean and spacious room
Reviewed on 19 Feb 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
8/10 Very Good! (1,000 reviews)
Very clean room. Staff was excellent. Very welcoming. Would and will stay there again, no question.
Reviewed on 22 Feb 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is 4.005.424 ₫ per night from 18 Mar to 19 Mar
4.005.424 ₫
5.324.069 ₫ total
18 Mar - 19 Mar
includes taxes & fees
8.4/10 Very Good! (616 reviews)
The hotel was exceptional! We love staying at soundview during the winter months!
Reviewed on 23 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.
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.
Osprey's Dominion
You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
McCabe's Beach
Why not spend a lazy afternoon at McCabe's Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.
