Southold

Travel Guide

A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.
A coastal landscape with a sunset, a marina, and a residential area.
A champagne bottle in a black bucket with a cork, a glass of champagne, and outdoor patio furniture with umbrellas.
A river with boats, a marina, and residential areas.
A vineyard with rows of grapevines and outdoor seating.
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is P11,676 per night from Nov 24 to Nov 25
P11,676
P14,914 total
Nov 24 - Nov 25
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! (351 reviews)
"The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing."

Reviewed on Nov 12, 2026

The Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
The price is P5,136 per night from Dec 13 to Dec 14
P5,136
P5,906 total
Dec 13 - Dec 14
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is P8,387 per night from Nov 23 to Nov 24
P8,387
P10,731 total
Nov 23 - Nov 24
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! (1,009 reviews)
"Great location. The restaurant / bistro is very good. Try the salmon. Staff accommodating and helpful. Room and facilities were clean and inviting. Would stay again."

Reviewed on Nov 9, 2026

Water's Edge Resort & Spa
See all 4,213 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 ...
Windward Shores Ocean Resort
North Fork Resort

North Fork 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 Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
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.

Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
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.
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Things to do

great fun with friends

Full Day Private Long Island Wine Tours from New York City

P11,842
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Southold
A coastal landscape with a lake, dense greenery, and a sunset sky.

Shelter Island

A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights