Southold

Travel Guide

Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Tranquil sunset seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Tranquil seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
White wooden lifeguard stand and rowboat on the beach at Sunken Meadow State Park New York
Aerial North Shore Long Island
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is RM1,269 per night from 1 Jun to 2 Jun
RM1,269
RM1,548 total
1 Jun - 2 Jun
includes taxes & fees
Stay at this hotel in Southold. Enjoy free Wi-Fi, free bicycles on-site and a business centre. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (273 reviews)
"We had such a beautiful stay! Can't wait to return!"

Reviewed on 30 May 2026

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
The price is RM1,851 per night from 4 Jun to 5 Jun
RM1,851
RM2,115 total
4 Jun - 5 Jun
includes taxes & fees
Stay at this business-friendly B&B in Southold. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Mattebella Vineyards and Croteaux Vineyards ...
9.8/10 Exceptional! (16 reviews)
"Location was perfect for visiting the wineries… breakfast was to die for!"

Reviewed on 22 Mar 2026

Vine & Sand
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 RM349 per night from 7 Jun to 8 Jun
RM349
RM402 total
7 Jun - 8 Jun
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8/10 Very Good! (1,003 reviews)
"We used the place as a crash pad - easy to get to from the marina and close to "the main strip" . We did not have a car and it was a holiday weekend."

Reviewed on 28 May 2026

Pier Blue Inn Old Saybrook - Essex
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 Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.2/10 Wonderful! (19 reviews)
"Clean rooms. On the smaller side, so one full room barely comfortably seats 4 ppl. the pool was nice. the staff was very nice. comes with an outdoor seating area and a grill and a fire pit."

Reviewed on 26 May 2026

North Fork Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Stay at this beach aparthotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End ...
9/10 Wonderful! (253 reviews)
"Beautiful property- we would definitely stay there again"

Reviewed on 23 May 2026

Cliffside Resort Condominiums
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway Amagansett NY
Stay at this beach aparthotel in Amagansett. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (313 reviews)
"Ocean view room had no view of the ocean"

Reviewed on 18 May 2026

Windward Shores Ocean Resort
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.

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