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 CA $211 per night from Apr 9 to Apr 10
CA $211
CA $276 total
Apr 9 - Apr 10
includes taxes & fees
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (250 reviews)
Clean, spacious and thoughtful room amenities. Close by to town and great restaurants.

Reviewed on Mar 23, 2026

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
Book a stay at this business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mattebella Vineyards and Croteaux ...
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!

Reviewed on Mar 22, 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
The price is CA $292 per night from Mar 30 to Mar 31
CA $292
CA $359 total
Mar 30 - Mar 31
includes taxes & fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,007 reviews)
The room was perfect, staff was excellent, parking was right next to my room. Best Breakfast Sausage ever.

Reviewed on Mar 24, 2026

Water's Edge Resort & Spa
See all 4,386 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
Book a stay at this beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
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 Mar 2, 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 WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
North Fork Cottages & RV Resort
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

Westbrook CT
Book a stay at this beach cottage in Westbrook. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Westbrook Town Beach and Clinton ...
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
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

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

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

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

CA $259
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Southold

Cities near Southold

Central Park summer

Shelter Island

Beautiful spot on the #longisland sound surfing

Greenport West