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
Aerial North Shore Long Island
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is ฿5,027 per night from 21 Feb to 22 Feb
฿5,027
฿5,743 total
21 Feb - 22 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! (242 reviews)
Clean and spacious room

Reviewed on 19 Feb 2026

The Shoals Suites and Slips
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is ฿4,648 per night from 23 Mar to 24 Mar
฿4,648
฿6,203 total
23 Mar - 24 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! (614 reviews)
Hotel complaints Extra unknown/ non-disclosed charges- 13 arrival and 15 checkout **there are more charges than shown in Expedia Rooms not matching pictures (told to have an ocean view when not the case) Some ice on road/ sidewalk (seen someone slip) Disappointing “continental” breakfast Parking ...

Reviewed on 15 Feb 2026

Sound View Greenport
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is ฿6,094 per night from 24 Feb to 25 Feb
฿6,094
฿7,546 total
24 Feb - 25 Feb
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (1,006 reviews)
The view of the ocean and gazebos were amazing. Everyone was so courteous and it wasn't a madhouse. Quiet and relaxing. The pool was also nice and warm

Reviewed on 18 Feb 2026

Water's Edge Resort & Spa
See all 4,340 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 ...
9/10 Wonderful! (5,064 reviews)
Room meet all my needs for a week long stay. Close to transit, etc., without the noise of Times Square. They were responsive when the room was too cold and brought heaters, too. Would stay here again!

Reviewed on 20 Feb 2026

Radio City Apartments
Sonder by Marriott Bonvoy Court Square Apartments Long Island City

Sonder by Marriott Bonvoy Court Square Apartments Long Island City

3.5 out of 5
45-06 Pearson Street Long Island City NY
Stay at this aparthotel in Long Island City. Enjoy concierge services, housekeeping and air conditioning. Popular attractions Grand Central Terminal and 5th ...
8.8/10 Excellent! (179 reviews)
Good hotel

Reviewed on 18 Feb 2026

Sonder by Marriott Bonvoy Court Square Apartments Long Island City
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 ...
8.4/10 Very Good! (980 reviews)
No staff I didn’t know that about this place

Reviewed on 16 Feb 2026

East Village Hotel
See all 37,352 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

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

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

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

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

Things to do

Private Luxury Wine Tours of Long Island Pindar Winery

Private Luxury Wine Tours of Long Island Pindar Winery

฿5,731
per adult
Private Luxury Wine Tours of Long Island Pindar Winery
Long Island Wine Tour North Fork Sights Bites Flights Half Day PM

Long Island Wine Tour North Fork Sights Bites Flights Half Day PM

฿10,793
per adult
Long Island Wine Tour North Fork Sights Bites Flights Half Day PM
See all activities in Southold