Southold, NY

Travel Guide

A calm lake with a forest in the background during sunset.
A calm lake with tall grasses in the foreground and a forested shoreline under a pink sky.
A river with red vegetation and a forest in the background.
A lifeguard tower, a boat, and a sandy beach with the ocean in the background.
A river with boats, a marina, and residential areas.
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is SAR 758 per night from Oct 1 to Oct 2
SAR 758
SAR 960 total
1 Oct - 2 Oct
includes taxes & fees
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (334 reviews)
"Our room was clean and very spacious, the bathroom was large and modern. They setup a food shed outside with a nice menu and bar where you can sit down and have fresh oysters for example and a drink when returning from the wineries all day. The staff outside was super friendly. However, here are ..."

Reviewed on 2 September 2026

The Shoals Suites and Slips
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is SAR 1,011 per night from Sep 28 to Sep 29
SAR 1,011
SAR 1,476 total
28 Sep - 29 Sep
includes taxes & fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (717 reviews)
"A Beautiful and Peaceful Stay at Sound View Greenport I had a wonderful stay at Sound View Greenport and would highly recommend it to anyone looking for a relaxing getaway on the North Fork of Long Island. It’s a great place for couples, families, or anyone who simply wants to escape the busy city ..."

Reviewed on 7 September 2026

Sound View Greenport
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 SAR 320 per night from Sep 8 to Sep 9
SAR 320
SAR 368 total
8 Sep - 9 Sep
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. ...
8/10 Very Good! (1,009 reviews)
"We decided to try this place due to the great location. When we arrived were told it has been recently sold to a new owner and renovations were started. However, the photo online looks like a totally different room, not our room. Our room was clean and staff were excellent, but very run down, and ..."

Reviewed on 7 September 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 WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.6/10 Exceptional! (53 reviews)
"My sisters and I booked a 2 bedroom cottage for a long weekend around Greenport. The listing said it was a 2 bedroom with queen beds but when I arrived I realized one room was only a full so one of us had to sleep on the pull out couch for us all to be comfortable. You also definitely need a car. ..."

Reviewed on 3 September 2026

North Fork Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
9/10 Wonderful! (290 reviews)
"Everything was wonderful to the check in to check out. Parking was a breeze. The view from room of the water was so nice. We definitely will be returning next time I want to go for longer stay."

Reviewed on 31 August 2026

Cliffside Resort Condominiums
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway Amagansett NY
Book a stay at this beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (322 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."

Reviewed on 11 August 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.

Stay near popular Southold attractions