Shelter Island House, Shelter Island Heights

Shelter Island House - A Historic Boutique Hotel with Pool, Garden Views, and Beach Proximity

Located just one block from Crescent Beach in Shelter Island Heights, Shelter Island House draws inspiration from its original 1800s roots while offering modern beach flair across its 10-11 rooms. This four-star property features spa bathrooms with oversized walk-in showers, garden views, and C.O. Bigelow bath amenities in each accommodation. The Shelter Island Heights hotel provides complimentary continental breakfast served on a sunny deck, along with amenities including free Wi-Fi, bicycles, beach chairs, umbrellas, and towels. Guests can dine at the on-site Tavern restaurant and Chez Marie, which serves small plates crafted from fresh local ingredients, or enjoy evening cocktails by the swimming pool after a game of pétanque on the lit bocce courts. Shelter Island House sits on a quiet street just half a kilometer from Sunset Beach and is accessible via ferry from Greenport or Sag Harbor.

Pros

The 19th-century property maintains its historic architecture while incorporating chic, modern design elements

Outdoor spaces include a swimming pool, wrap-around porch with wicker furniture, and gardens with private patios

Bocce courts lit by strings of white lights offer evening entertainment

On-site restaurant features a chef who sources ingredients from local farmers and fishermen

Continental breakfast is included with the stay

Cons

The hotel requires a non-refundable $150 deposit per dog (maximum 2 dogs under 50 lbs) and pets are only allowed in designated pet-friendly rooms

Located 52.5 miles from Long Island MacArthur Airport, requiring transportation arrangements