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
White wooden lifeguard stand and rowboat on the beach at Sunken Meadow State Park New York
Aerial North Shore Long Island
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is CA $529 per night from Jul 8 to Jul 9
CA $529
CA $640 total
Jul 8 - Jul 9
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! (288 reviews)
"Beautiful property on the water very relaxing excellent room"

Reviewed on Jun 20, 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 CA $127 per night from Jul 7 to Jul 8
CA $127
CA $146 total
Jul 7 - Jul 8
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. ...
8/10 Very good! (1,001 reviews)
"staff and parking"

Reviewed on Jun 22, 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is CA $705 per night from Jul 1 to Jul 2
CA $705
CA $927 total
Jul 1 - Jul 2
includes taxes & fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very good! (658 reviews)
"The Soundview is one of my favorite hotels in greenport ( favorite) we had an amazing room I never wanted to leave!!"

Reviewed on Jun 20, 2026

Sound View Greenport
See all 4,428 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.
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Southold NY
Book a stay at this beach vacation home in Southold. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Custer Institute and Observatory and ...
10/10 Exceptional! (39 reviews)
"Lovely home in Southold! Comfortable beds, adequate 2 baths… third was a great outdoor shower. Kitchen had everything we needed. Very nice furnishings and linens. Outdoor spaces were fantastic!"

Reviewed on Jun 22, 2026

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country

Peconic NY
Stay at this cottage in Southold. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Goldsmith's Inlet Park and Sannino's Bella Vita Vineyard ...
10/10 Exceptional! (186 reviews)
"Excellent Host. Prime location to vineyards and beaches"

Reviewed on May 26, 2026

Fabulous Waterfront Property in the Heart of Wine Country
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' ...
9.2/10 Wonderful! (24 reviews)
"Excellent place definitely love it. Definitely a little expensive for one night on the weekend but I love it and definitely would go back the cleanest place absolutely atmosphere people will break full was great. Highly recommend."

Reviewed on Jun 20, 2026

North Fork 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

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

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

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

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

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 $262
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

Peconic and Great Peconic bay meet at Nassau Point drone view

Greenport West