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Reviewed August 17, 2018 via mobile

More pros than cons: not perfect for the price. The unit we stayed in is very nice - #42. Best views, nicely decorated , I love it all. The stove (oven) doesn’t work and that was a pain with 3 kids. Nothing major -but at 5k for 5 nights, things should work.
The beach is pristine - absolute perfection. The men on the beach taking care of towels & chairs are excellent. So efficient and friendly. It’s a pleasure to chat and tip them (probably not necessary but we always do) . Thx guys!
The pool is a sore spot for me. It is the perfect temperature and very clean - BUT depending on who you are and how long you’ve been coming to Windward shores has a direct effect on how you are treated.
If you’ve been there for years - your kids can jump in the pool and bring in floats. If not, zero tolerance for jumping and floats. Sounds silly - but not to an 11 year old Who has been watching other kids jump like crazy, for hours.
When I complained about a wicked woman berating my son I was told “ well we know her “ .
It’s odd and unfair -but we got thru it and met some lovely like minded people and made the best of it. Pool was beautiful and quiet.
Housekeeping is hit or miss. We had to ask on day 3 to please change the super sandy sheets - and of course we left her a nice tip. They didn’t do much else unless asked, but then all was fine.
The upstairs loft area very nice - but needs a separate AC unit, it was 86 degrees up there with the main a/c unit on high blast. Tough sleeping.
That being said - it’s a beautiful serene resort - there just needs to be more consistency with staff and housekeeping.

Date of stay: August 2018
Trip type: Traveled with family
Thank jeaninct
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed August 10, 2018 via mobile

My boyfriend and I booked this trip and we were really excited about it after a long stretch of no vacation time and working over time. However, there’s no telling with the weather and right before, I saw it was forecast to be non stop showers with thunderstorms throughout the entire weekend. I saw online there was a no refund policy but also saw on the booking site rescheduling/cancellation varied by rooms. To double check, I called to talk to somebody, thinking I would inquire about refund policy or what’s the process of a reschedule or just cancel. I just wanted to know my options if any. I didn’t beg for a refund, I’m perfectly fine with policy and just wanted clarification, to talk to someone instead of email. The manager’s voice seemed to change from friendly to defensive as I brought up the forecasted poor weather and asked me where I had seen thunderstorms reported. I told her I had seen it on news12 on the tv while at the gym that morning, and checked weather channels website. She started to disagree with me stating she too had watched it and not seen any thunderstorms forecasted. I cited I had seen it and it had obviously made me think about canceling this weekend, but she kept pushing and stating how she had checked the weather too and watched the forecast. She sounded defensive, and her tone seemed to imply I was lying. I stated “I’m not lying about the weather and I know forecasts are subjective, always changing.” She cited that Long Island has varying weather across the island but kept insisting on how she didn’t know where I heard thunderstorms. By that point, I was put off. I’m not trying to start anything but I shouldn’t feel under scrutiny when I call to inquire more about policies. I spent the majority of the phone call defending my usage of weather forecasts than learning about how I can plan for the one weekend I get to go to the beach. I wouldn’t lie about the weather especially when I wanted to go in the first place. After i said “I’m just trying to ask about rescheduling policy” she finally told me I’d get a refund if someone else books that night, however I was just really thrown off by the tone I had received that I decided not to go and not to bother with the refund. I’m including the screenshot weather forecast because for some odd reason I feel the need to verify myself after that conversation.

Date of stay: August 2018
Trip type: Traveled as a couple
1  Thank emmam1114
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed April 23, 2018 via mobile

I have stayed here about 4 times. But this time we were upgraded to apt 45, which was great. Plenty of sunlight and space.The kitchen and bathrooms were all modern. All types of utensils provided for every type of cooking or baking. I believe it is one of the biggest apartment. We enjoyed sitting on the balcony watching the sunrise and set. We plan on returning again this year. The pool was closed to the weather and the tennis courts were under construction.

Date of stay: April 2018
Trip type: Traveled with family
Thank missbimsha
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
windwardmanager, General Manager at Windward Shores, responded to this reviewResponded April 24, 2018

Thank you for your positive remarks. I am so pleased you enjoyed you assigned unit and the views!

Tennis court renovations are almost complete and the pool opens on 5.25.18. We hope come back afterward to use all of the facilities!

Kind Regards,
Laurie
Manager

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This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed February 2, 2018

Although outdated, the hotel is in a prime location between Montauk and Amaganset. Our room included two bedrooms and a lovely deck overlooking the ocean. We were traveling with another couple for a wedding, but are very interested in returning next summer with our young daughter.

Room tip: Book a room facing the ocean.
Date of stay: September 2017
  • Trip type: Traveled as a couple
    • Value
    • Rooms
    • Service
Thank ckaplowitz
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
windwardmanager, General Manager at Windward Shores, responded to this reviewResponded February 10, 2018

Thank you for the very nice review you posted recently. It is always great to hear our guests enjoy their time here. I passed on your comments to our staff and they, too, are very appreciative of your kind words.

We hope to have the occasion to welcome you back to Windward Shores Ocean Resort!

Laurie, Manager
Team Windward

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This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed September 14, 2017 via mobile

We spent a lovely week here at Windward Shores. It is situated right on a beautifully beach with chairs and umbrellas provided. The rooms are clean and the decor up to date. The pool and grounds are well manicured. My only complaint, and it is significant, is that the bed is terrible. Please, get new mattresses! I recommend this hotel despite the beds.

Date of stay: September 2017
Trip type: Traveled as a couple
Thank Jackies55
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
windwardmanager, General Manager at Windward Shores, responded to this reviewResponded September 16, 2017

Thank you so much for taking the time to offer feedback re your recent stay at Windward Shores. I apologize about your experience with bed in the unit you occupied and assure you that it was new, deemed to be a good bed and, actually, quite pricey. I wish there was a bed that universal appeal. Of course, I will pass on your comment to the owner of that unit. I hope to have the occasion to welcome you back to Windward Shores.

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This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
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