Best Hotels in Town of Southold Town for 2025

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. Enjoy features like free breakfast, plus a 24-hour gym and concierge services.

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.

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 restaurant, a bar and a coffee shop/cafe.

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 2 restaurants.

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 American Beech Hotel. During your stay, you're just a quick walk from Greenport Farmers' Market. 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.

During your stay at Hotel Moraine, you'll be close to Greenport Carousel. You'll find features such as free breakfast and free self-parking, plus a restaurant.

Our customers tell us that they can't get enough of the helpful staff at Greenporter Hotel. 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 24-hour gym.

During your stay at this holiday home, you'll be close to The Old Field Vineyards. You'll find features such as a water park, laundry facilities and an arcade/games room. Free WiFi and a kitchen are available in the holiday home.

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

During your stay at this holiday home, you'll be within walking distance of Sparkling Pointe. You'll find features such as laundry facilities. The holiday home offers a kitchen and 3 bathrooms.

During your stay at this holiday home, you'll be close to McCall Wines. You'll find features such as a water park, laundry facilities and an arcade/games room. The holiday home offers a private pool and a kitchen.

During your stay at this villa, you're just a quick walk from Orient By The Sea Marina. Enjoy features like an outdoor pool and laundry facilities. Enjoy your stay with amenities like a private pool and a kitchen in the villa.

During your stay at this cottage, you're just a quick walk from Oysterponds Historical Society. Features include laundry facilities. The cottage includes amenities such as a kitchen and 2 bathrooms.