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 4.889.887 ₫ per night from 26 Nov to 27 Nov
4.889.887 ₫
6.245.746 ₫ total
26 Nov - 27 Nov
includes taxes & fees
9.4/10 Exceptional! (221 reviews)
This was a stunning place to stay in all respects. The large room was wonderrful. Thank you!
Reviewed on 8 Nov 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is 2.666.516 ₫ per night from 3 Dec to 4 Dec
2.666.516 ₫
3.066.494 ₫ total
3 Dec - 4 Dec
includes taxes & fees
7.6/10 Good! (1,007 reviews)
Staff was kind. Easy, comfortable stay.
Reviewed on 19 Nov 2025
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is 4.225.829 ₫ per night from 8 Dec to 9 Dec
4.225.829 ₫
6.118.093 ₫ total
8 Dec - 9 Dec
includes taxes & fees
8.4/10 Very Good! (593 reviews)
Amazing views and comfy bed and room. No sound privacy between the rooms at all! I guess they o relooked sound insulation in an otherwise gorgeous renovation of a roadside motel.
Reviewed on 19 Nov 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.
Custer Institute and Observatory
Enjoy an outing to Custer Institute and Observatory during your stay in Southold. Wander the beaches and gardens while you're in the 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.
