Find the Cheap Shelter Island Hotels

With a stay at The Rams Head Inn in Shelter Island Heights, you'll be 4.9 mi (7.9 km) from Sunset Beach and 5.8 mi (9.3 km) from The Hamptons Beaches. This inn is 6.6 mi (10.6 km) from Kontokosta Winery and 6.8 mi (11 km) from 67 Steps Beach. Take advantage of recreation opportunities such as a private beach or take in the view from a terrace and a garden. Additional amenities at this inn include complimentary wireless internet access, tour/ticket assistance, and a picnic area. Grab a bite to eat at one of the inn's many dining establishments, which include 2 restaurants and a coffee shop/cafe. Quench your thirst with your favorite drink at the bar/lounge. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 17 air-conditioned guestrooms. Complimentary wireless internet access is available to keep you connected. Bathrooms feature shower/tub combinations, complimentary toiletries, and hair dryers.

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 1.2 mi (1.9 km) from Sunset Beach and 1.3 mi (2.1 km) from Crescent 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.

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 1.1 mi (1.8 km) from Sunset Beach and 1.4 mi (2.2 km) from Crescent 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.

Located in Greenport, Stirling House Bed & Breakfast is on the waterfront, within a 15-minute walk of East End Seaport Maritime Museum and Railroad Museum of Long Island. This bed & breakfast is 1.2 mi (1.9 km) from Kontokosta Winery and 2 mi (3.2 km) from Island's End Golf and Country Club. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access, concierge services, and a fireplace in the lobby. Grab a bite from the snack bar/deli serving guests of Stirling House Bed & Breakfast. Wrap up your day with a drink at the bar/lounge. A complimentary full breakfast is included. Featured amenities include express check-in, express check-out, and complimentary newspapers in the lobby. Free self parking is available onsite. Treat yourself to a stay in one of the 3 guestrooms, featuring fireplaces and flat-screen televisions. Cable programming and iPod docking stations are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include complimentary newspapers and minibars, and housekeeping is provided daily.

When you stay at American Beech Hotel in Greenport, you'll be in the historical district, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach. This inn is 5.1 mi (8.2 km) from Mashomack Preserve and 6.4 mi (10.3 km) from The Hamptons Beaches. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and wedding services. You can enjoy a meal at the restaurant serving the guests of American Beech Hotel, or stop in at the snack bar/deli. Wrap up your day with a drink at the bar/lounge. A complimentary on-the-go breakfast is served daily from 9:00 AM to 9:30 AM. Featured amenities include express check-in, express check-out, and multilingual staff. Make yourself at home in one of the 11 individually decorated guestrooms, featuring refrigerators and flat-screen televisions. Cable programming along with iPod docking stations are provided for your entertainment. Private bathrooms have designer toiletries and hair dryers. Conveniences include safes and minibars, and housekeeping is provided daily.

When you a stay at The Menhaden in Greenport, you'll be near the beach, just steps from Camera Obscura and Greenport Carousel. This hotel is 0.2 mi (0.3 km) from Greenport Farmers' Market and 0.2 mi (0.4 km) from Railroad Museum of Long Island. Take in the views from a rooftop terrace and make use of amenities such as complimentary wireless internet access and concierge services. This hotel also features shopping on site, wedding services, and a reception hall. 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 self-serve breakfast is served daily from 8:00 AM to 11:00 AM. Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and luggage storage. This hotel has 2 meeting rooms available for events. Limited parking is available onsite. Stay in one of 16 guestrooms featuring Smart televisions. Your memory foam bed comes with down comforters and premium bedding. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with bathtubs or showers feature rainfall showerheads and designer toiletries.

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.

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 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.