Southold Travel Guide

Tourist Guide

Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Tranquil sunset seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Tranquil seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod.
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is Rp2.841.702 per night from 3 Feb to 4 Feb
Rp2.841.702
Rp3.246.643 total
3 Feb - 4 Feb
includes taxes & fees
Stay at this hotel in Southold. Enjoy free Wi-Fi, free bicycles on-site and a business centre. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (238 reviews)
Room was great. Clean and comfortable. Glad I found this place and will be back.

Reviewed on 22 Jan 2026

The Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.8/10 Good! (1,000 reviews)
I have stayed here a number of times, and each time the room has been spotless and smells fresh. The staff is very friendly and always offers to help in some way, whether it's to get the snow off my car or provide bottled water. I will be staying here again!

Reviewed on 23 Jan 2026

Get rates
Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is Rp2.251.506 per night from 3 Feb to 4 Feb
Rp2.251.506
Rp3.051.863 total
3 Feb - 4 Feb
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.4/10 Very Good! (608 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on 10 Jan 2026

Sound View Greenport
See all 4,322 properties in Southold
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.
Radio City Apartments

Radio City Apartments

3.5 out of 5
142 West 49th Street New York NY
Stay at this aparthotel in New York. Enjoy free Wi-Fi, a 24-hour front desk and a business centre. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (5,004 reviews)
Clean room and good service

Reviewed on 29 Jan 2026

Radio City Apartments
East Village Hotel

East Village Hotel

3 out of 5
147 1st Ave New York NY
Stay at this aparthotel in New York. Enjoy free Wi-Fi, daily housekeeping and premium TV channels. Our guests praise the helpful staff and the clean rooms in ...
8.2/10 Very Good! (968 reviews)
The room was in a great location.

Reviewed on 27 Jan 2026

East Village Hotel
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
Stay at this cabin in Catskill. Enjoy free parking, furnished patios and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park are ...
9.4/10 Exceptional! (137 reviews)
The room was better than expected. Simple but everything you needed was there. Looking forward to our next stay :)

Reviewed on 25 Jan 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all 37,378 properties in New York
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

Cleanest, prettiest winery on the east end of Long Island! Try the Cuvee' Rose!

Sparkling Pointe

You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.

Sparkling Pointe

Horton Lane Beach

Why not spend a lazy afternoon at Horton Lane Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.

Horton Lane Beach

Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Sannino's Bella Vita Vineyard

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.

Croteaux Vineyards

The Old Field Vineyards

You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets in this family-friendly area.

The Old Field Vineyards

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.

Osprey's Dominion

Cities near Southold

Sunset along the beach at Towd Point in Southampton, Long Island, New York.

Peconic