Southold, NY

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 AED 691 per night from Mar 30 to Mar 31
AED 691
AED 789 total
includes taxes & fees
30 Mar - 31 Mar
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! (149 reviews)
"great location and view"

Reviewed on 19 March 2025

The Shoals Suites and Slips
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
The price is AED 694 per night from Mar 30 to Mar 31
AED 694
AED 862 total
includes taxes & fees
30 Mar - 31 Mar
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (1,001 reviews)
Excellent stay
"It was a lovely one night stay with a friend. The room was beautiful, the hotel was stunning, and the check in was great. Lots of recommendations for good places to go. Very pleasant experience!"

Reviewed on 26 March 2025

Water's Edge Resort & Spa
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 AED 253 per night from Mar 30 to Mar 31
AED 253
AED 291 total
includes taxes & fees
30 Mar - 31 Mar
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. ...
7.6/10 Good! (932 reviews)
"Cozy and clean hotel. The staff were very nice. We really enjoyed our stay. There is a good breakfast/lunch restaurant across the street."

Reviewed on 21 March 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,261 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.
North Fork 7 Bedroom Farmhouse Escape
North Fork 7 Bedroom Farmhouse Escape
3 out of 5
Southold
Stay at this vacation home in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions The Old Field Vineyards and Horton Point Park are located ...
9.4/10 Exceptional! (3 reviews)
Convenient location, multi bedroom
"We were in town for a wedding with small children in tow- the house was perfectly located for us to get to wedding events in under 10 minutes but do be aware that it’s on a busy road. The house is set back so there wasn’t too much traffic noise, especially with the window AC units going. You could ..."

Reviewed on 7 August 2022

North Fork 7 Bedroom Farmhouse Escape
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! (275 reviews)
"Great cozy place"

Reviewed on 4 March 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! (207 reviews)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"

Reviewed on 5 November 2024

Cliffside Resort Condominiums
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

Cleanest, prettiest winery on the east end of Long Island! Try the Cuvee' Rose!

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

The Old Field Vineyards

You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets in this family-friendly area.

The Old Field Vineyards

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

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