Top Condo Resorts in Town of Southold Town in 2026

A white colonial-style house with a green roof and a lighthouse tower.

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Top Town of Southold Town Hotel Reviews

Beach, Pool, Wine, Shopping!

10/10 Excellent

"Beautiful property, plenty of space. Stayed with a toddler and 4 adults."

The Shoals Suites and Slips

10/10 Excellent

"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. Looking forward to return in the near future."

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

8/10 Good

"Pat is a wonderful owner with a lovely property that sits at the end of the road. The backyard is what he refers to as a creek. There are a few canoes that you could use for recreation or to get to the local public beach. There are many bicycles available. When we were there in early August, there were several gnats/bugs and it was very humid. I wish there would’ve been a pool or at least some lounge chairs with shade. His beach umbrella was broken. Overall, he was a pleasure to work with and there are many vineyards to choose from."

The Menhaden

10/10 Excellent

"Definitely stay here! A perfect location, walkable to so many cute restaurants and shops. Beautiful water view from the rooftop. Most comfortable bed and gorgeous, clean room. And the icing on the cake (almost literally!) is the snack room on each floor with fresh baked cookies, fresh juices, chips, candies and more. They make a wonderful espresso martini at the bar too. We hope to be back!"

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Top Town of Southold Town Hotel Reviews

Beach, Pool, Wine, Shopping!

Cliffside Resort Condominiums

The Shoals Suites and Slips

Aqua Vista

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Charming Mattituck Retreat Near the Bay with Modern Updates

The Harbor Front Inn

The Menhaden

The SandPiper

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