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 £132 per night from 11 Feb to 12 Feb
£132
11 Feb - 12 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
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
Stay at this business-friendly B&B in Southold. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Croteaux Vineyards and Corey Creek Winery ...
9.6/10 Exceptional! (15 reviews)
Vine + Sand was wonderful. The hosts were so friendly and it was close to many wineries.

Reviewed on 19 Jan 2026

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Vine & Sand
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is £145 per night from 8 Mar to 9 Mar
£145
8 Mar - 9 Mar
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! (609 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 4,320 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.
The SandPiper

The SandPiper

Greenport, NY
Stay at this holiday home in Greenport. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Railroad Museum of Long Island and East End Seaport ...
9.6/10 Exceptional! (32 reviews)
The host was very understanding about some last minute events that affected our trip

Reviewed on 26 Jan 2026

The SandPiper
Aqua Vista

Aqua Vista

Greenport, NY
Stay at this holiday home in Greenport. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Railroad Museum of Long Island and East End Seaport ...
9.8/10 Exceptional! (24 reviews)
This place was a dream. Super comfortable. The host has thought of everything, including a sweet holiday welcome gift. Everything is in walking distance- I didn't use my car for 2 days. It was wonderful to walk along the water into town. What a great retreat!

Reviewed on 2 Jan 2026

Aqua Vista
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays NY
Stay at this beach holiday home in Hampton Bays. Enjoy a beach locale, a garden and laundry facilities. Popular attractions Meschutt Beach and Good Ground Park ...
9.4/10 Exceptional! (130 reviews)
We absolutely loved the place and had a great time. There was plenty of space for the kids to spread out and enjoyed the indoor fireplace. The sunrise views were amazing and it's always special to stay on the water. Communication with the owner was great. We hope to visit again.

Reviewed on 11 Jan 2026

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
See all 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.

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

Central Park summer

Shelter Island