Search Best Hotels in Southold

When you stay at The Shoals Suites and Slips in Southold, you'll be near the bay, within a 5-minute drive of The Old Field Vineyards and Mattebella Vineyards. This hotel is 3 mi (4.8 km) from Railroad Museum of Long Island and 3.1 mi (5 km) from Greenport Carousel. Make use of convenient amenities such as concierge services, shopping on site, and wedding services. Additional features at this hotel include a communal living room, a picnic area, and a ballroom. Enjoy a meal at the restaurant or snacks in the hotel's coffee shop/cafe. Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 8:30 AM to 10:30 AM. Featured amenities include a business center, luggage storage, and a safe deposit box at the front desk. Make yourself at home in one of the 20 individually decorated guestrooms, featuring kitchenettes with ovens and stovetops. Your bed comes with down comforters and premium bedding. Rooms have private furnished balconies or patios. 43-inch flat-screen televisions with Netflix provide entertainment, while complimentary wireless internet access keeps you connected.

When you stay at Cliffside Resort Condominiums in Greenport, you'll be near the beach, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach. This beach aparthotel is 8.2 mi (13.1 km) from The Hamptons Beaches and 2 mi (3.2 km) from Eastern Long Island Hospital. Enjoy recreation amenities such as a seasonal outdoor pool or take in the view from a terrace. This aparthotel also features complimentary wireless internet access, a picnic area, and barbecue grills. Featured amenities include laundry facilities and a vending machine. Free self parking is available onsite. Make yourself at home in one of the 68 guestrooms, featuring kitchenettes with refrigerators and stovetops. Rooms have private furnished balconies. Complimentary wireless internet access keeps you connected, and flat-screen televisions are provided for your entertainment. Conveniences include phones, as well as separate sitting areas and microwaves.

Located in Greenport, Hotel Moraine is within a 5-minute drive of Kontokosta Winery and 67 Steps Beach. This beach hotel is 2.1 mi (3.4 km) from Greenport Carousel and 2.2 mi (3.5 km) from Safe Harbor Stirling. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including a 24-hour fitness center and a seasonal outdoor pool. This hotel also features wedding services, a fireplace in the lobby, and a banquet hall. Enjoy a meal at the restaurant or snacks in the coffee shop/cafe. The hotel also offers room service (during limited hours). Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. Featured amenities include dry cleaning/laundry services, luggage storage, and a safe deposit box at the front desk. Planning an event in Greenport? This hotel has 800 square feet (74 square meters) of space consisting of conference space and meeting rooms. Free self parking is available onsite. Make yourself at home in one of the 20 guestrooms featuring minibars and LED televisions. Digital television is provided for your entertainment. Private bathrooms with showers feature rainfall showerheads and complimentary toiletries. Conveniences include safes and desks, and housekeeping is provided daily.

When you stay at Silver Sands Motel & Beach Bungalows in Greenport, you'll be on the waterfront, within a 5-minute drive of Railroad Museum of Long Island and Greenport Carousel. This beach hotel is 1.2 mi (1.9 km) from East End Seaport Maritime Museum and 1.2 mi (2 km) from Greenport Farmers' Market. Take advantage of recreation opportunities such as a private beach or take in the view from a terrace and a garden. Additional features at this hotel include complimentary wireless internet access, concierge services, and a picnic area. Grab a bite to eat at one of the hotel's many dining establishments, which include 2 restaurants and a coffee shop/cafe. Need to unwind? Take a break with a tasty beverage at one of the 2 bars/lounges. Self-serve breakfasts are available daily from 8:00 AM to 1:00 PM for a fee. Featured amenities include complimentary wired internet access, a 24-hour front desk, and laundry facilities. Planning an event in Greenport? This hotel has 700 square feet (65 square meters) of space consisting of conference space and meeting rooms. Guests may use a ferry terminal shuttle for a surcharge, and free self parking is available onsite. Make yourself at home in one of the 36 individually decorated guestrooms, featuring minibars and Smart televisions. Your pillowtop bed comes with down comforters and premium bedding. Complimentary wired and wireless internet access keeps you connected, and digital programming provides entertainment. Bathrooms have hair dryers and bathrobes.

When you stay at Shelter Island House in Shelter Island Heights, you'll be next to a golf course, within a 10-minute walk of Shelter Island Country Club and Sunset Beach. This golf hotel is 4.3 mi (6.9 km) from The Hamptons Beaches and 0.5 mi (0.8 km) from Crescent Beach. Enjoy recreational amenities such as a seasonal outdoor pool and bicycles to rent. Additional features at this hotel include complimentary wireless internet access, concierge services, and a picnic area. Enjoy a meal at the restaurant, or stay in and take advantage of the hotel's room service (during limited hours). Unwind at the end of the day with a drink at the bar/lounge or the poolside bar. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. Featured amenities include complimentary wired internet access, luggage storage, and a safe deposit box at the front desk. Free self parking is available onsite. Make yourself at home in one of the 11 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Bathrooms have separate bathtubs and showers and designer toiletries. Conveniences include safes and irons/ironing boards, and housekeeping is provided daily.

With a stay at The Chequit in Shelter Island Heights (The Heights), you'll be within a 5-minute drive of Shelter Island Country Club and Sylvester Manor. This hotel is 4.8 mi (7.8 km) from The Hamptons Beaches and 1.1 mi (1.8 km) from Sunset Beach. Enjoy a meal at the restaurant or snacks in the hotel's coffee shop/cafe. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 35 guestrooms. Complimentary wireless internet access is available to keep you connected. Bathrooms with showers are provided. Conveniences include blackout drapes/curtains, housekeeping is provided on request, and irons/ironing boards can be requested.

With a stay at House on Chase Creek in Shelter Island Heights (The Heights), you'll be within a 5-minute drive of Shelter Island Country Club and Sylvester Manor. This golf guesthouse is 4.5 mi (7.2 km) from The Hamptons Beaches and 1.2 mi (1.9 km) from Sunset Beach. Take advantage of recreation opportunities such as bicycles to rent or take in the view from a terrace and a garden. Featured amenities include a 24-hour front desk and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 4 air-conditioned guestrooms. Complimentary wireless internet access is available to keep you connected. Conveniences include ceiling fans and irons/ironing boards, and housekeeping is provided daily.

A stay at Greenporter Hotel places you in the heart of Greenport, within a 5-minute walk of Railroad Museum of Long Island and Camera Obscura. This hotel is 6.2 mi (9.9 km) from The Hamptons Beaches and 0.2 mi (0.3 km) from Greenport Carousel. Enjoy a range of recreational amenities, including a spa tub, a 24-hour fitness center, and a seasonal outdoor pool. Featured amenities include a business center, express check-out, and an elevator. Planning an event in Greenport? This hotel has 275 square feet (26 square meters) of space consisting of conference space and 2 meeting rooms. Free self parking is available onsite. Make yourself at home in one of the 34 air-conditioned rooms featuring flat-screen televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature designer toiletries and hair dryers.