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 $512 per night from Aug 12 to Aug 13
CA $512
CA $619 total
Aug 12 - Aug 13
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! (191 reviews)
"The hotel was lovely"

Reviewed on Aug. 9, 2025

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25, Southold, NY
Stay at this 3-star business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mattebella Vineyards and Croteaux ...
10/10 Exceptional! (9 reviews)
"Beautiful house and trip to stay in the North Fork. Hosts are incredible. Highly recommend!!"

Reviewed on Jul. 23, 2025

Get rates
Vine & Sand
Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St, Riverhead, NY
The price is CA $145 per night from Aug 17 to Aug 18
CA $145
CA $166 total
Aug 17 - Aug 18
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! (678 reviews)
"ROOMS ARE VERY COZY !"

Reviewed on Aug. 7, 2025

Greenview Inn Riverhead
See all 4,319 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, 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! (290 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
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! (233 reviews)
"Great location, great views. Walls are a little thin."

Reviewed on Aug. 4, 2025

Cliffside Resort Condominiums
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)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"

Reviewed on Aug. 4, 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 $203
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 $190
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Southold

Cities near Southold

Photo by tom owens

Shelter Island

Photo by Nina Dinoff

Greenport West