Boutique hotel holiday rentals in Shelter Island Heights

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.

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".

Downtown Mystic Suite with fireplace, king, futon

Located in the heart of downtown Mystic in the Historic District, this charming suite offers everything you need for a relaxing stay. This 600 sq ft suite has a king bed, futon, fireplace, kitchenette and private bath. There is a beautiful brick terrace and gardens behind the Carriage House with a fire pit, bbq, and plenty of seating. Leave you car behind as everything Mystic has to offer is just a short 3 minute walk. There is off street parking as well.

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 -- Debbie'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.

Cove Ledge Marina Room 2E on Water w/ Pool & Kayak

Located at Cove Ledge Marina, this newly renovated one-room unit is just steps away from the tranquil waters of the marina and includes complimentary access to the outdoor pool and recreation areas, as well as a complimentary kayak rental.