Boutique hotel vacation rentals in Shelter Island Heights

Hero King Deluxe, Hero Beach Club, Beachfront

Indulge in an extraordinary experience at our exquisite beachside property while enjoying the rest of Montauk's nearby places. Just a stone's throw away from your beachside retreat lies the Second House Museum. Ready for some outdoor adventure? Head over to Fort Pond Bay Park or Ditch Plains Beach. Make your way to Deep Hollow Ranch, the oldest working cattle ranch in the United States. No visit to Montauk would be complete without going to Montauk Point State Park and Montauk Point Lighthouse.

Spectacular 2 Bath King Suite in Historic Mansion

Enjoy a luxurious experience when you stay in the Master Suite at Ludington House. Ascend the Grand Staircase to the second floor to find the showpiece of the nine bedroom mansion. The private suite features His and Hers Bathrooms/Dressing Room and a four post King Bed. Outside your suite you have use of the "morning room"; a charming light-filled living area filled with local art and literature that is shared with one other guestroom. The adjoining foyer has a small kitchenette for beverages.

Bellport Village Temperance Hall: Old Inlet Suite

A quaint, seaside village located on the South Shore of Long Island, Bellport Village has long been a destination for both day trippers and summer residents. It offers a variety of shopping and dining experiences, along with one of the most well-known summer theatres in the region, the Gateway Playhouse. Bellport is one of the rare municipalities with its own golf course, private Fire Island ocean beach lovingly referred to as "Ho-Hum Beach" as well as a bay side beach named "Mother's Beach".

Bellport Village Temperance Hall: The Ho-Hum Suite

A quaint, seaside village located on the South Shore of Long Island, Bellport Village has long been a destination for both day trippers and summer residents. It offers a variety of shopping and dining experiences, along with one of the most well-known summer theatres in the region, the Gateway Playhouse. Bellport is one of the rare municipalities with its own golf course, private Fire Island ocean beach lovingly referred to as "Ho-Hum Beach" as well as a bay side beach named "Mother's Beach".

Somewhere in the Hamptons

Southampton LI Hotel - Your Next Vacation Destination. Conveniently located, only minutes from the world's famous Cooper's Beach and charming Village of Southampton with numerous restaurants, cafes and boutiques - Southampton Long Island Hotel will be your favorite lodging choice in the Hamptons. Open all year long - it is perfect for the summer beach getaway, business retreat, relaxing tour of exceptional wineries or just for a well deserved relaxing weekend as a treat for yourself.

Bellport Inn Enchanting Garden Suite - 2 bedrooms

This enchanting suite at Bellport Inn welcomes you through an inviting porch into a sunlit kitchenette. The primary bedroom offers a queen size bed, pull out full size sofa bed and an ensuite bath. A window lined second bedroom offers a queen size bed and a private bath with clawfoot tub. A shared garden oasis includes an outdoor grill for guest use.

Luxury Lifestyle Hotel, Greenport Village, NY

Located in the heart of Greenport Village, The Menhaden is a boutique hotel with high-end service and modern amenities. Enjoy the North Fork’s only hotel roof deck and easy access to all the North Fork has to offer, including local vineyards and the beach. Less than two hours from New York City, visit us by train, Jitney, boat or car.

The Lin Beach House -- Edie's Room

Play. Sip. Stay. Welcome to the Guest House and sister hotel of Matchbook Distilling Co. Here you can find the traditional vineyard and beach resort reimagined into a guest house, where creativity, relaxation and indulgence can all be found in equal measure.

The Lin Beach House - Theresa's Suite

Play. Sip. Stay. Welcome to the Guest House and sister hotel of Matchbook Distilling Co. Here you can find the traditional vineyard and beach resort reimagined into a guest house, where creativity, relaxation and indulgence can all be found in equal measure.

The Lin Beach House -- Lillian's Suite

Play. Sip. Stay. Welcome to the Guest House and sister hotel of Matchbook Distilling Co. Here you can find the traditional vineyard and beach resort reimagined into a guest house, where creativity, relaxation and indulgence can all be found in equal measure.

The Lin Beach House -- Jane's Suite

Play. Sip. Stay. Welcome to the Guest House and sister hotel of Matchbook Distilling Co. Here you can find the traditional vineyard and beach resort reimagined into a guest house, where creativity, relaxation and indulgence can all be found in equal measure.

Southampton Long Island Hotel

Southampton Long Island Hotel - Your Southampton Escape. Conveniently located, only minutes from the world's famous Cooper's Beach and charming Village of Southampton. All rooms feature private baths, air conditioning, cable TV. Wireless Internet.