Southold

Travel Guide

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
Southold
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is S$251 per night from 5 May to 6 May
S$251
5 May - 6 May
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! (257 reviews)
Beautiful property near a picturesque town. I would definitely recommend. I’d love to return soon!

Reviewed on 5 Apr, 2026

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
The price is S$502 per night from 13 Apr to 14 Apr
S$502
13 Apr - 14 Apr
includes taxes & fees
Stay at this business-friendly B&B in Southold. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Mattebella Vineyards and Croteaux Vineyards ...
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!

Reviewed on 22 Mar, 2026

Vine & Sand
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is S$393 per night from 14 Apr to 15 Apr
S$393
14 Apr - 15 Apr
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! (1,000 reviews)
Enjoyable stay.

Reviewed on 28 Mar, 2026

Water's Edge Resort & Spa
See all 4,369 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.
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway Amagansett NY
Stay at this beach aparthotel in Amagansett. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (310 reviews)
When I went to the property it was not shoveled. A challenge to get to the room. I enjoyed the room with minor things that could change.

Reviewed on 2 Mar, 2026

Windward Shores Ocean Resort
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
North Fork Cottages & RV Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Stay at this beach aparthotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End ...
9/10 Wonderful! (249 reviews)
The unit was cute and well-appointed. I would recommend a new refrigerator in the unit, as the freezer door was broken.

Reviewed on 12 Nov, 2025

Cliffside Resort Condominiums
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

Sparkling Pointe

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

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

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

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

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

Corey Creek Winery

You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Corey Creek Winery

Things to do

great fun with friends

Full Day Private Long Island Wine Tours from New York City

S$242
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Southold
Central Park summer

Shelter Island

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