Southold

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 P17,799 per night from Sep 1 to Sep 2
P17,799
P21,866 total
Sep 1 - Sep 2
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! (318 reviews)
"The hotel was very clean with a lovely environment. The staff (especially at the front desk) were helpful, friendly, polite and very knowledgeable about recommendations for the area. The property was well maintained and the views were beautiful and very accessible to many activities in the area. ..."

Reviewed on Aug 14, 2026

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
Book a stay at this business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mattebella Vineyards and Croteaux ...
9.8/10 Exceptional! (20 reviews)
"The hosts were very friendly and welcoming. They were always available when we had questions or needed anything. We enjoyed the fresh pastries and fresh fruit the 1st morning. They were very accommodating and had breakfast out early when we had to leave extra early for our event our 1st day."

Reviewed on Jun 24, 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 P6,025 per night from Aug 16 to Aug 17
P6,025
P6,928 total
Aug 16 - Aug 17
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. ...
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' ...
9.4/10 Exceptional! (46 reviews)
"The property was so clean, charming, and exceeded all expectations. The whole staff was so lovely and helped solve every issue above and beyond! We got locked out of our room and the front desk was closed but there was an after hours number that we were able to call and they virtually unlocked our ..."

Reviewed on Aug 13, 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 ...
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 Aug 11, 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

Things to do