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 4.457.575 ₫ per night from 20 Apr to 21 Apr
4.457.575 ₫
5.751.055 ₫ total
20 Apr - 21 Apr
includes taxes & fees
9.4/10 Exceptional! (259 reviews)
Beautiful space in Southold
Reviewed on 11 Apr 2026
Vine & Sand
47100 New York 25 Southold NY
The price is 10.547.381 ₫ per night from 13 Apr to 14 Apr
10.547.381 ₫
12.050.383 ₫ total
13 Apr - 14 Apr
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
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is 6.137.756 ₫ per night from 17 Apr to 18 Apr
6.137.756 ₫
7.512.629 ₫ total
17 Apr - 18 Apr
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
it was our first time and we really enjoyed the place. The Band was amazing! Being at the resort made our weekend great. Will definitely be back!
Reviewed on 11 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.
Popular places to visit
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.
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.
