Bed and Breakfast and Inn in Southold, NY

This guest house is located in the Shelter Island Heights district, offering excellent value and a convenient base for exploring the island.
This accommodation provides a cozy room with a comfortable queen bed, a modern walk-in shower, air conditioning, and Wi-Fi, ideal for two guests seeking an authentic island experience.

This Southold ground-floor apartment offers stunning panoramic views of the Long Island Sound and Pond, situated directly opposite Southold Town Beach.
The self-catering apartment sleeps four guests in two bedrooms and boasts three bathrooms, a private patio, and access to complimentary beach equipment, electric car charging, and bicycles, plus in-unit laundry facilities.

This studio apartment is located in Shelter Island Heights, offering convenient access to local attractions and amenities.
This studio offers accommodation for up to four guests with a king bed, a full-size sleeper sofa, a separate bathroom, a private deck, and a wetbar-style kitchenette with a half-size refrigerator and sink.

This studio apartment is situated in Greenport Village, a short 300-metre walk from Mitchell Park Marina, local boutiques, and the Shelter Island Ferry terminal.
This 93-square-metre studio offers a king bed and sofa bed for up to four guests, featuring air conditioning, a seasonal outdoor pool with harbour views, and complimentary bicycles for exploring the area.

Cowgirl Palace is located in Sag Harbor, a short drive from Wainscott, with Montauk Point Lighthouse 14 miles away and Second House Museum 19 miles away. The property has excellent ratings for location, cleanliness, and overall user experience.
The guesthouse offers a comfortable and convenient stay with a private bathroom, air conditioning, and a flat-screen TV. Guests can enjoy a range of amenities, including a swimming pool, a hot tub, a tennis court, a garden, and a terrace.

This guest house in Shelter Island Heights offers a water view, situated close to the district's local attractions.
This property accommodates two guests in one bedroom with a king-sized bed and a private en-suite bathroom, featuring air conditioning, complimentary Wi-Fi, and a garden.

ZEY HOTEL is situated in Greenport, a charming village on Long Island's North Fork, just 26 miles from Splish Splash water park and 48 miles from Long Island MacArthur Airport. The hotel has received very good user ratings, with excellent marks for its location and cleanliness.
This one-bedroom guesthouse features a private bathroom with bathrobes, slippers, and a hairdryer. Guests can enjoy a range of amenities, including a terrace, garden, picnic area, lounge, and free bikes.

This apartment is located in Greenport, on the waterfront, with direct access to a private beach and is situated on a 22.5-hectare property close to the Mashomack Preserve, offering 18 kilometres of coastline. The apartment features a king-sized bed, a sitting area, a private balcony overlooking the beach, and access to an outdoor pool, yoga classes, and a restaurant, all within the 14-acre property.

This charming bed and breakfast is situated in a central Greenport neighbourhood, just a short walk from the town's restaurants, shops, cafes, and beaches, with Preston's Dock for harbour tours just a short distance away. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The private suite offers a relaxing retreat for two guests, featuring a comfortable queen-size bed, a separate dressing room, and a modern bathroom with a rain shower head. Amenities include a wet bar, mini fridge, electric tea kettle, pour-over coffee filter, and a front porch with views of the neighbourhood.

This Southold guesthouse is ideally located within a 1.6km walk of Mattebella, Corey Creek, and Croteaux Vineyards, with Osprey's Dominion and Sannino's Bella Vita Vineyard also within a 1.6km radius.
The 111 square metre property offers one bedroom, one bathroom, sleeping up to two guests, and features a swimming pool, hot tub, terrace, garden, and parking, plus complimentary breakfast.

Harbor Knoll Bed and Breakfast is situated in Greenport, a short distance from the town's beaches and within easy reach of attractions like Splish Splash, just 26 miles away. The property enjoys excellent ratings for location, cleanliness, and overall guest satisfaction.
The guest house offers comfortable accommodation with a choice of rooms featuring a private bathroom and a floor area of 21 square meters. Guests can enjoy a variety of amenities, including a swimming pool, a tennis court, a garden, a terrace, and a bar, as well as free Wi-Fi and parking.

This newly renovated one-bedroom suite is located in the peaceful Nassau Point area of Cutchogue, a short walk (less than 1km) from Fisherman's Beach and within 8km of over 20 wineries.
The self-contained apartment, sleeping two, features a private entrance, compact kitchenette, Wi-Fi, and a private outdoor seating area with fire pit; nearby beaches include Causeway Beach (1.6km) and Point Beach (2.4km).