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 4.954.178 ₫ per night from 29 Apr to 30 Apr
4.954.178 ₫
6.318.599 ₫ total
29 Apr - 30 Apr
includes taxes & fees
9.4/10 Exceptional! (261 reviews)
The room was spacious. I’m very clean. I was very impressed. Location easy to get in and out of highly recommend.
Reviewed on 14 Apr 2026
Vine & Sand
47100 New York 25 Southold NY
The price is 9.495.166 ₫ per night from 19 Apr to 20 Apr
9.495.166 ₫
10.848.226 ₫ total
19 Apr - 20 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 6.586.080 ₫ per night from 29 Apr to 30 Apr
6.586.080 ₫
8.028.349 ₫ total
29 Apr - 30 Apr
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Front desk staff were amazing! The bar staff were very attentive and friendly. Rooms are clean, but definitely dated.
Reviewed on 13 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.
