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 AU$416 per night from 16 Oct to 17 Oct
AU$416
16 Oct - 17 Oct
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! (209 reviews)
"Great quick stay"

Reviewed on 28 Sept 2025

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 AU$140 per night from 12 Oct to 13 Oct
AU$140
12 Oct - 13 Oct
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (1,002 reviews)
"I will go there forever now being that it's just it if the way but close enough to kokomos"

Reviewed on 2 Oct 2025

Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is AU$163 per night from 2 Nov to 3 Nov
AU$163
2 Nov - 3 Nov
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! (1,005 reviews)
"Overall, a nice hotel for a one day trip! :)"

Reviewed on 5 Oct 2025

Quality Inn Old Saybrook - Westbrook
See all 4,321 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.
Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country

Peconic
Book a stay at this family-friendly cottage in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions Goldsmith's Inlet Park and Sannino's ...
9.8/10 Exceptional! (172 reviews)
"Great place and beautiful scenery"

Reviewed on 31 Aug 2025

Fabulous Waterfront Property in the Heart of Wine Country
Beautifully farmhouse

Beautifully farmhouse

Southold
Book a stay at this family-friendly vacation home in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions Sparkling Pointe and The Old ...
10/10 Exceptional! (2 reviews)
"We spent a few days to attend a family wedding. We were 7 and the house was extremely comfortable for all of us. The house is 2 floors and there is no bathroom upstairs so keep that in mind when assigning sleeping arrangements. We found a well stocked welcome basket and a bottle of wine which were ..."

Reviewed on 8 Sept 2025

Beautifully farmhouse
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! (296 reviews)
"The non ocean view rooms are fabulous. I’m sure the ocean side ones are great."

Reviewed on 30 Sept 2025

Windward Shores Ocean 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

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

Activities

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

AU$221
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

AU$210
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 Erisa Dilo

Shelter Island Heights