Southold Travel Guide

Tourist Guide

A calm lake with a forest in the background during sunset.
A calm lake with tall grasses in the foreground and a forested shoreline under a pink sky.
A river with red vegetation and a forest in the background.
A lifeguard tower, a boat, and a sandy beach with the ocean in the background.
A river with boats, a marina, and residential areas.
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is ₹17,523 per night from 27 Oct to 28 Oct
₹17,523
₹22,382 total
27 Oct - 28 Oct
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! (347 reviews)
"We had a 2 bedroom. It was tight in the rooms. It met our needs for a couple of nights. I thought it was expensive based on its location behind a boat marina."

Reviewed on 20 Oct 2026

The Shoals Suites and Slips
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is ₹17,837 per night from 1 Nov to 2 Nov
₹17,837
₹22,148 total
1 Nov - 2 Nov
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! (1,001 reviews)
"Great"

Reviewed on 21 Oct 2026

Water's Edge Resort & Spa
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 ₹7,719 per night from 23 Nov to 24 Nov
₹7,719
₹8,877 total
23 Nov - 24 Nov
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8/10 Very good! (1,002 reviews)
"Staff was friendly. Grounds very well kept. But rooms are very dated."

Reviewed on 22 Oct 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,294 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 ...
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 Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.6/10 Exceptional! (69 reviews)
"What a great place , hidden gem on North Fork! it would have been nice if the Resturant was opened. We will be back"

Reviewed on 21 Oct 2026

North Fork 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! (297 reviews)
"Great condo. Very nice location and grounds."

Reviewed on 11 Oct 2026

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.
See properties

Cities near Southold

An aerial view of a harbor with boats, a ship, and a dock extending into the water.

Greenport

A wooden gazebo by a pond with a large tree trunk nearby.

Shelter Island

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