Southold Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Benny Goh
Top hotels in Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is 4.446.572 ₫ per night from 12 Jan to 13 Jan
4.446.572 ₫
5.080.208 ₫ total
12 Jan - 13 Jan
includes taxes & fees
9.4/10 Exceptional! (234 reviews)
The room was much larger than expected, very clean. Perfect location, Melissa at the front desk was very helpful
Reviewed on 1 Jan 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is 6.014.914 ₫ per night from 12 Jan to 13 Jan
6.014.914 ₫
7.370.239 ₫ total
12 Jan - 13 Jan
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Great place!
Reviewed on 31 Dec 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,002 reviews)
Parking was very convenient, and the property is pet-friendly with a nice grassy area in the back for pets to relieve themselves. The room was clean and staff were friendly, although queen size bed felt like twin xl but overall, a pleasant and hassle-free stay.
Reviewed on 31 Dec 2025
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.
Horton Point Park
Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.
