Southold Travel Guide

Tourist 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 £341 per night from 20 Jul to 21 Jul
£341
20 Jul - 21 Jul
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! (288 reviews)
"Beautiful property on the water very relaxing excellent room"

Reviewed on 20 Jun 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 £77 per night from 7 Jul to 8 Jul
£77
7 Jul - 8 Jul
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! (1,001 reviews)
"staff and parking"

Reviewed on 22 Jun 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 £573 per night from 19 Jul to 20 Jul
£573
19 Jul - 20 Jul
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
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 20 Jun 2026

Sound View Greenport
See all 4,467 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
Stay at this beach holiday home in Southold. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Custer Institute and Observatory and Croteaux ...
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 22 Jun 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 Wi-Fi, 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 26 May 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 Wi-Fi, 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 20 Jun 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

Custer Institute and Observatory

Enjoy an outing to Custer Institute and Observatory during your stay in Southold. Wander the beaches and gardens while you're in the area.

Custer Institute and Observatory

Things to do

great fun with friends

Full Day Private Long Island Wine Tours from New York City

£140
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