Boutique hotel holiday rentals in Shelter Island Heights

Hero Queen, Hero Beach Club, Steps from the Beach

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.

American Beech - Petite King Room 7

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scenery, and return to a memorable and comfortable room at the end of your day. The boutique hotel features eleven suites, including two, double-bedroom apartments. Our guests pay a resort fee of $35 per night, including additional taxes at check in.

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".

A Wave Inn, Deluxe Studio

Unwind and relax by the poolside or spend time in the scenic nature at A Wave Inn in Montauk. Located in this popular tourist district, we’re ranked one of the best Montauk hotels. Our completely renovated spaces now provide guests with even more comfort and hospitality for enjoying their stay. Your room charge will be paid prior to your arrival. The remaining balance of taxes (8.625% + 3% ) will be charged upon arrival. A refundable security deposit of $XX will also be collected.

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.

Sun 'N' Sound, Bayfront Studio Lower

Exclusive waterfront resorts make any vacation memorable, especially at a place like Sun N’ Sound. The hotel tops hospitality expectations by all measures. The large accommodations are designed for comfortable long term stays. You’ll feel right at home during your time in our comfy guest rooms.

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.

Cottage Room at Topping Rose House

Topping Rose House is the most charming estate in the entire Hamptons. With a classic mansion from the 1840s overlooking the property, Topping Rose House blends the history of Bridgehampton with the new, crisp feel of contemporary design.