Southold

Travel 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 HK$1,191 per night from 1 Mar to 2 Mar
HK$1,191
HK$1,361 total
1 Mar - 2 Mar
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
Fully refundable
The price is HK$1,162 per night from 25 Mar to 26 Mar
HK$1,162
HK$1,551 total
25 Mar - 26 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! (615 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 HK$1,527 per night from 24 Feb to 25 Feb
HK$1,527
HK$1,891 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! (1,007 reviews)
Everything was wonderful Very nice staff Room was very clean Bed was comfy View was wonderful

Reviewed on 21 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.
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! (25 reviews)
Love the place stairs are a bit tricky if you have trouble with normal ones

Reviewed on 15 Feb 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 ...
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
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 ...
9.8/10 Exceptional! (32 reviews)
The host was very understanding about some last minute events that affected our trip

Reviewed on 26 Jan 2026

The SandPiper
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

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

great fun with friends

Full Day Private Long Island Wine Tours from New York City

HK$1,471
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Southold
Central Park summer

Shelter Island