Best Hotels in Town of Southold Town for 2026

Our customers tell us that they can't get enough of the helpful staff at Sound View Greenport. During your stay, you'll be close to East End Seaport Maritime Museum. Features include free breakfast and free WiFi in public areas, plus 2 bars.

During your stay at Zey Hotel, you're just a quick walk from Greenport Farmers' Market. You'll find features such as free WiFi in public areas and free self-parking, plus a bar.

Our customers tell us that they can't get enough of the helpful staff at The Shoals Suites and Slips. During your stay, you're just a quick walk from The Old Field Vineyards. Enjoy features like a bar, a coffee shop/cafe and a business centre.

During your stay at North Fork Resort, you'll be within walking distance of Kontokosta Winery. You'll find features such as free WiFi in public areas and free self-parking, plus laundry facilities. This comfortable cottage has 40 cottages. All cottages offer free WiFi and patios.

Our customers tell us that they can't get enough of the helpful staff at The Harbor Front Inn. During your stay, you're just a quick walk from Camera Obscura. Free breakfast, free WiFi in public areas and a 24-hour gym are available.

During your stay at Cliffside Resort Condominiums, you'll be close to Railroad Museum of Long Island. Enjoy features like free WiFi in public areas and free self-parking, plus laundry facilities. This comfortable aparthotel has 68 apartments over 2 floors. Each apartment includes amenities such as free WiFi and a kitchenette.

Our customers tell us that they can't get enough of the helpful staff at The Menhaden. During your stay, you're just a quick walk from Camera Obscura. Free breakfast, free WiFi in public areas and a restaurant are available.

Our customers tell us that they can't get enough of the helpful staff at Silver Sands Motel & Beach Bungalows. During your stay, you'll be within walking distance of Railroad Museum of Long Island. Features include free WiFi in public areas and free self-parking, plus 3 restaurants.

Our customers tell us that they can't get enough of the helpful staff at American Beech Hotel. During your stay, you're just a quick walk from Greenport Harbor Brewing Company. Enjoy features like free breakfast and free WiFi in public areas, plus a restaurant. This property offers pet-friendly amenities, such as food and water bowls.

Our customers tell us that they can't get enough of the helpful staff at Oyster Estate. During your stay, you're just a quick walk from Railroad Museum of Long Island. Enjoy features like free WiFi in public areas and free self-parking, plus a gym.

During your stay at this holiday home, you'll be close to Custer Institute and Observatory. Enjoy features like laundry facilities. The holiday home offers free WiFi and a kitchen.

During your stay at Vine & Sand, you're just a quick walk from Mattebella Vineyards. Features include free breakfast, free WiFi in public areas and free self-parking.

During your stay at this cottage, you'll be within walking distance of Railroad Museum of Long Island. You'll find features such as laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the cottage.

During your stay at Stirling House Bed & Breakfast, you're just a quick walk from Greenport Harbor Brewing Company. Features include free breakfast, free WiFi in public areas and free self-parking.

During your stay at Harbor Knoll Bed & Breakfast, you're just a quick walk from Railroad Museum of Long Island. You'll find features such as free WiFi in public areas and free self-parking, plus a bar.