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 HK$2,282 per night from 6 Jul to 7 Jul
HK$2,282
HK$2,803 total
6 Jul - 7 Jul
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! (174 reviews)
"Third stay here, always a pleasure and so close to my favorite southold vineyards"

Reviewed on 1 Jul 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 Croteaux Vineyards and Corey Creek ...
10/10 Exceptional! (7 reviews)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport."

Reviewed on 17 Feb 2025

Get rates
Vine & Sand
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is HK$867 per night from 16 Jul to 17 Jul
HK$867
HK$997 total
16 Jul - 17 Jul
includes taxes & fees
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,002 reviews)
"Great location and pool, close to a wonderful restaurant"

Reviewed on 30 Jun 2025

Quality Inn Old Saybrook - Westbrook
See all 4,376 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! (286 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
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! (224 reviews)
"Quiet"

Reviewed on 23 Jun 2025

Cliffside Resort Condominiums
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 WiFi, free parking, and an outdoor pool. Popular attractions Cooper's Beach and Meschutt Beach are ...
Canoe Place Waterfront Residences
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

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 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

Things to do

Half Day Private Long Island Wine Tour Experience

Half-Day Private Long Island Wine Tour Experience

HK$2,284
per adult
Half-Day Private Long Island Wine Tour Experience
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

HK$1,248
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
great fun with friends

Full Day Private Long Island Wine Tours from New York City

HK$1,484
per adult
Full Day Private Long Island Wine Tours from New York City
Vetted Flights and food pairings at local winery.

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

HK$2,661
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM
Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

HK$4,388
per adult
Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day
Fun at North Fork Vineyards

Private Guided Wine Country Bike Tour in Mattituck

HK$1,562
per adult
Private Guided Wine Country Bike Tour in Mattituck
See all activities in Southold
Photo by tom owens

Shelter Island