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
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 RM663 per night from 31 Mar to 1 Apr
RM663
RM758 total
31 Mar - 1 Apr
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! (245 reviews)
Fine

Reviewed on 15 Mar 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 Mattebella Vineyards and Croteaux Vineyards ...
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
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is RM525 per night from 1 Apr to 2 Apr
RM525
RM672 total
1 Apr - 2 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! (1,002 reviews)
We loved our stay here. The staff was so wonderful! (Mary Luz at the Starbucks was so sweet!) and the food was fresh and delicious. The waitstaff was attentive and cognizant and caring regarding food allergies. The views from every vantage were special and memorable. We had not great weather and ...

Reviewed on 18 Mar 2026

Water's Edge Resort & Spa
See all 4,371 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
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

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

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

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

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