I have stayed here many times. If you want to get away to a sleepy village in the middle of Winter, then here you should go. Windward Shores is in Amagansett & borders Montauk. In February there is nothing to do but eat at John's Pancakes, shop at Go Local & relax. In the Summer this is a whole different... More

We recommended Windward Shores to our wedding guests, etc., and reservations were lost, double-charged, etc. Some guests advised of 2 night minimums, others were able to book a single night stay. The management were combative, disorganized and extraordinarily dishonest. GM Ken Kalafut lied to us on several points, making this a nightmare weekend. The topper: A group of our guests... More

Looked for a place in Montauk for a Saturday but couldn't find one. The Windward was on the way and the price was right. $95 for a Saturday night for a studio which we took advantage of by having our breakfast in.. It was a comfortable room with a complete kitchen. It was very clean but in need of updating.... More

After reading other cautionary reviews, I called to request a renovated room off season, which was not honored. The best thing I can say about my unrenovated room was that it was basic. Mine had crumbs on all of the dining room chairs and sink counter, cobwebs in the corners, and missing patches of plaster on the ceiling. The stench... More

We usually stay in Montauk, but found it too loud and busy when we were there in July. So we tried Napeague “Stretch” in Amagansett on Labor Day. Good location as it was quiet and only 5 minutes or so in either direction to Amagansett or Montauk restaurants and shoppes. We stayed at Windward Shores and it was wonderful. We... More

Loved Windward Shores! Many times out in Amagansett and East Hampton, but this was our first time at Windward Shores. Loved it! I saw recommendations posted by reviewers to request a renovated room, which we did. It was in the ocean building and we had a view of the dunes. The kitchen even had a dishwasher! Lovely room. The beach... More

We just made our fourth visit to Windward Shores. The previous three were over the past 5 years. It is a very nice place to stay. The location is fantastic. It is literally right on the ocean, on one of the most beautiful beaches you can imagine, and there is a nice, heated swimming pool, and two hard surface tennis... More

We stayed in a studio unit for six nights. The hotel is located on a beautiful beach (dunes) and provides free lounges and umbrellas. Their is also a very nice large pool and pretty landscaping around the complex. Our only disappointment was in our first floor studio. Apparently each unit is individually owned. Our unit was in great need of... More

My fiance and I have stayed here twice over the last year and we love it. The owners are great (we left a few items behind and they gladly sent them to us) and the unit we usually stay in is beautiful. Quiet, great getaway with a nice little kitchen for romantic nights in and a great location (two words:... More