Southold Travel Guide

Tourist 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 ฿12,108 per night from 24 Aug to 25 Aug
฿12,108
฿14,648 total
24 Aug - 25 Aug
includes taxes & fees
Stay at this 3.5-star hotel in Southold. Enjoy free Wi-Fi, free bicycles on-site and a business centre. Our guests praise the helpful staff in their reviews. ...
9.4/10 Exceptional! (192 reviews)
"The hotel was lovely"

Reviewed on 9 Aug 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 Wi-Fi 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 23 Jul 2025

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Vine & Sand
Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St, Riverhead, NY
Stay at this motel in Riverhead. Enjoy free Wi-Fi, 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 20 Aug 2025

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Greenview Inn Riverhead
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 Wi-Fi, 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 20 Aug 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 Wi-Fi, 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 28 Jun 2025

Windward Shores Ocean Resort
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

4 out of 5
239 E Montauk Hwy, Hampton Bays, NY
Stay at this 4-star spa condo in Hampton Bays. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Cooper's Beach and Meschutt Beach are ...
Canoe Place Waterfront Residences
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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

฿4,848
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

฿4,553
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM

Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM

฿11,104
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM
See all activities in Southold