Hotels in Shelter Island Heights

Superior Queen Guestroom

Bespoke suites boasting modern amenities, land marked distinction and luxe charm. A designated landmark hotel and restaurant are the embodiment of 18th century seaside charm-Located in the most coveted location in the Hamptons. Room features Free WiFi, Free Local Calls, Telephone, TV, Room Services, Minibar, Coffeemaker, Wake up calls, Private Bathroom, Self Controlled AC/Heating, Alarm Clock, Hairdryer, Iron/Ironing Board. This is a Non Smoking Room. Max Occupancy of 2 guests per Guestroom.

Frette bedding and private deck or yard

Our one bedroom cottages feature a queen bed, and most feature a half bathroom in addition to a full bathroom. The spacious and luxurious living room features a small kitchen with a dishwasher, refrigerator/freezer along with downdraft cooktop and microwave, and is equipped with glassware, flatware, tableware and more. All of our One Bedroom Cottages offer private decks which feature sofas and chairs for lounging and relaxing among the trees and nature to complete the perfect escape.

Hampton Bays Hotel, King Suite - Adults Only

Hampton Bays Hotel on Main is a boutique hotel in the heart of town, featuring comfortable, affordable rooms above the Rod and Reel and Bub's Tavern. Enjoy a contactless stay with online check-in and secure smart locks with personalized access codes, designed to ensure guest privacy and convenience. Located close to beaches, dining, and nightlife, our hotel provides a high-quality experience at the center of it all, perfect for exploring the vibrant charm of the Hamptons.

Long Island Sound Views | Free Breakfast & Pool

Wake up to the waves at Sound View Greenport. Every room boasts a private waterfront deck overlooking the Long Island Sound. Unwind on our quarter-mile private beach, lounge by the seasonal pool, or savor local seafood at The Halyard. Just minutes from North Fork wineries and downtown Greenport, this mid-century modern retreat offers the perfect mix of relaxation and adventure. End your day with a cocktail at the Piano Bar and a stunning sunset.

Partial Harbor Views + Free Breakfast & Pool

Wake up to harbor views at The Harbor Front Inn, perfectly set in the heart of Greenport Village. Just steps from Mitchell Park Marina, boutique shops, and the Shelter Island Ferry, this stay blends coastal charm with modern comfort. Enjoy the seasonal outdoor pool, start your mornings with complimentary breakfast, and take advantage of free parking while exploring Long Island Wine Country and the North Fork’s best spots.

The Pridwin

Our corner preferred room offers a king bed and queen sleeper sofa, windows on two sides with full water views of Crescent Beach and Shelter Island Sound, full bathroom with stall shower, in-room Nespresso machine, beverage chiller, Beach Plum Farm bath amenities, safe, and free wifi.

Three Ducks

A thoughtfully designed guest room with vaulted ceilings, ample storage, and a window bench overlooking a private garden. Natural materials reflect the surrounding landscape, while a king bed ensures a restful stay. Enjoy Flamingo Estate bath products, luxury linens, and bathrobes.

A Room at the Beach

Bay king room with a king bed featuring Frette bedding, decor and art by Lucy and Charles Lemonides, flatscreen smart TV, complimentary wifi, gourmet minibar, chilled beverages, Nespresso maker, spa shower with garden access, and front deck and private back garden seating.

Waves and Sunset

Escape to our relaxing Oceanfront retreat where beach days and sunset nights await. Enjoy direct beach access with complimentary chairs and umbrellas, a sparkling pool, cozy beach bonfires under the stars, fully equipped kitchenettes perfect for easy coastal living.

Journey East Hampton

The Atlantic king suite features a spacious studio layout with stylish furnishings, a king bed, and a sofa bed. Amenities include an LED flat-screen TV, mini-fridge, grab-and-go breakfast, and access to a heated saltwater pool and serene garden.

Penthouse Bungalow with Oceanview

Enjoy this Penthouse Unit located at the Breakers at Montauk featuring a king sized bed, kitchenette, oversized and luxurious bathroom, on-site pool, private walk to the ocean, walk to Downtown and much more!

Ruschmeyers

The Ruschmeyer double queen room features natural wood details, vintage accents, and a breezy coastal layout with two queen beds, perfect for small groups or families exploring Montauk.