Southold

Travel Guide

Southold
Photo by Benny Goh
Photo by Benny Goh
Photo by Benny Goh
Photo by Benny Goh
Photo by 4 Star Traveler
Photo by 4 Star Traveler
Photo by 4 Star Traveler
Photo by 4 Star Traveler
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is CA $507 per night from Aug 26 to Aug 27
CA $507
CA $615 total
Aug 26 - Aug 27
includes taxes & fees
Stay at this 3.5-star hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (192 reviews)
"The hotel was lovely"

Reviewed on Aug. 9, 2025

The Shoals Suites and Slips
Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St, Riverhead, NY
The price is CA $155 per night from Sep 22 to Sep 23
CA $155
CA $178 total
Sep 22 - Sep 23
includes taxes & fees
Stay at this motel in Riverhead. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Splish Splash Water Park and Riverhead Raceway ...
7.2/10 Good! (702 reviews)
"Always my choice when staying in the area. Staff very friendly. Check in is quick and easy. Not to mention the newly renovated rooms."

Reviewed on Aug. 20, 2025

Greenview Inn Riverhead
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is CA $224 per night from Sep 21 to Sep 22
CA $224
CA $291 total
Sep 21 - Sep 22
includes taxes & fees
Book a stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (913 reviews)
"Nice place. Recommend."

Reviewed on Aug. 18, 2025

The Atlantic Hotel
See all 4,307 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.
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
Stay at this 3-star beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
8.8/10 Excellent! (238 reviews)
"Had a great time. Will be back"

Reviewed on Aug. 20, 2025

Cliffside Resort Condominiums
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway, PO Box 7031, Amagansett, NY
Stay at this 3-star beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (291 reviews)
Decent and Better priced
"A good choice for “affordable” stays in the Hamptons. The place is not “fresh” or chic by any means but it’s very acceptable and half the price of many other accommodations. Over all it’s a good value. Clean, well located and homey."

Reviewed on Jun. 28, 2025

Windward Shores Ocean Resort
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 out of 5
Bridgehampton
Stay at this vacation home in Bridgehampton. Enjoy free WiFi, a garden, and patios. Popular attractions The Hamptons Beaches and Channing Daughters Winery are ...
9.6/10 Exceptional! (12 reviews)
"Great property, wonderful condition of the interior as well as the exterior of the home. The water was always hot and the AC always cold. Every appliance worked properly as it should. The shower water pressure was a little low and the floor retained water but would stay again in a heartbeat!"

Reviewed on Aug. 5, 2025

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
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

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

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

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

Horton Point Park

Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Horton Point Park

Things to do

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

CA $204
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

CA $191
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Southold

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