Windward Shores

What is great about this place is that you can walk out your back door and go right onto a private ocean beach. All other resorts we have gone to do not offer this convenience or quality and privacy of the beach.
Rooms are nice and service is good. There is a well maintained pool with lifeguard and tennis courts. Great for families– my kids insist on going here every year. Conveniently located to East Hampton, Amagansett and Montauk.

I stayed here the weekend before Christmas to visit family who live in the area. The rooms are but nice for the price; the basic ones are small efficiencies with mini kitchens and fold-​out couches (in addition to the queen size beds). I found the bathrooms to be nice and more than serviceable.
Like others have mentioned, the rooms are on the beach, so you have quick and easy ocean access; however, you can’t really see the ocean (from the ground floor rooms) because the sand dunes serve as a buffer /​barrier protecting the buildings from being swept away /​over-​run when the tide is high or during storm swells.
The town of East Hampton is about 8 miles to the East. Montauk is about 2.5 miles to the West. Amagansett town proper is about 1.5 miles to the East. Windward Shores has some good places to eat at nearby during prime tourist season (Clam Bar, Lobster Lunch and Luz Deli) but only Luz Deli is open during the off-​season. Astro Pizza in Amagansett town is also a good close-​by dining option (open during off-​season).
I heard the hotel lounge is a bit too rustic or run down (with a shabby ping pong table); however, I did not venture in to check it out. The pool and tennis courts were closed this time of year (Winter /​off-​season). Prices range from $ 190 — $ 370. Most rooms are priced between $ 200– to $ 250. If you want a relatively inexpensive way to be near Montauk or the East Hampton this is very much a very good option. Perhaps deserves 2.5 or maybe 3.5 stars but I think 3 is a fair assessment.

This place is fantastic! Everything is clean and updated. The facilities are simple and welcoming. Everything you need for a beach getaway. I think Evan R’s review is somewhat inaccurate. While Windward Shores is certainly located in the middle of the Napeague Stretch there are several restaurants located on the stretch. In fact the Clam Bar is just a short walk to the east of the entrance to Windward Shores. The Lobster Roll is maybe a quarter mile to the west and there a few others within a mile including Cyril’s and Espo’s surf shop. If you do stay here you will not be in the middle of town but I would assume that is what you were looking for if you booked here and took a brief look at a map. The center of Montauk town is 5.9 miles away and Amagansett town is less than a 10 minute drive to the west. If you love the ocean this is a fantastic spot!

It’s a place to sleep.
I don’t know what other people’s rooms looked like but let me sum up ours: tube tv (complete with VHS), little stains on the bath towels, 90s furniture… desperately needs updating.
We didn’t choose this place as we were out here on a job and the client paid for it but… this place could be so great but instead it’s just bare minimum with a beautiful view and great beach access.
They do clean your room but when we got in bed there was sand at the foot of the bed in with the sheets… so apparently they just make the bed, not change the sheets…
We had a little kitchen/​fridge/​stove which was nice but other than that, it’s just a place to stay with a pool. Waking up to pounding feet: the kids above us running back and forth through their room. And let’s not forget the ol pull out queen size bed with springs that might as well be on the outside of it.
Would it kill people to update a LITTLE?!

Went to this place last year for a summer getaway. The rooms are basic but nice — every one has a small kitchen, fairly comfortable bed and average-​sized bathroom.
The best part is that it’s literally right on the beach, so you have easy ocean access. There’s not much a view from most rooms though, since you look right out at sand dunes.
As a cyclist, I loved that this was on a long main road, but for everyone else, it probably sucks. It’s at least three miles to Montauk proper, and about 2.5 miles from downtown Amagansett. So, a very easy car ride, but there’s literally nothing on foot within a few miles.
The «lounge» is kind of run down and has a shabby ping pong table. But, there’s a decent pool and tennis courts. Prices range from $ 190 — $ 370, but most rooms are between $ 200-​$ 250. If you want a relatively cheap way to be near Montauk or the Hamptons, this is a solid option.