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Windward Shores

2062 Montauk Highway, Amagansett, NY 11930
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Windward Shores
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Windward Shores
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42 reviews from our community

Traveler rating
    17
    12
    8
    2
    3
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11
14
Solo
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2
Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    3.5 of 5 stars
  • Rooms
    4 of 5 stars
  • Service
    4 of 5 stars
  • Value
    3.5 of 5 stars
  • Cleanliness
    4 of 5 stars
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Bronx, New York
Top Contributor
107 reviews 107 reviews
9 hotel reviews
29 helpful votes 29 helpful votes
4 of 5 stars Reviewed 3 weeks ago

Went here over Thanksgiving weekend with my bf and a few friends. What a nice place! And very reasonable off season. Everything in our room was new with a full kitchen. Very comfortable. Excellent location. Will definitely be back!

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New York City, New York
Senior Reviewer
6 reviews 6 reviews
4 hotel reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed October 20, 2014 via mobile

I was recommended to Windward by Sea crest as they were sold out for Columbus weekend, AND IM SO HAPPY THAT I CALLED. Sea crest was a very lovely place but I think I found my Favorite resort! The property is much smaller but that’s what gives it its charm. The Landscaping was beautiful. I had a studio with a... More 

Was this review helpful? Yes 1
2 reviews
5 of 5 stars Reviewed September 30, 2014 via mobile

As I pulled into Windward Shores in Amagansett, the first thing I noticed was the resort was spotless and beautifully landscaped. A half-hour into my mid-week September stay, I knew I had found my own paradise. Check-in was a breeze; the professional and friendly front-desk staff explained the layout of the resort, took time and care to answer my questions... More 

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ManagerWindward, General Manager at Windward Shores, responded to this review

Dear Cindyv2395: Thank you for the glowing feedback you provided regarding your recent stay at Windward Shores! I am thrilled you enjoyed your time with us so much and will make sure to share your review with our staff members. Please come back soon! All the Best, Laurie Costello General Manager More 

New York
Reviewer
4 reviews 4 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed September 25, 2014

I usually got to West Hampton, but it's just gotten too busy. Checked options online and found Windward. This place delivers peace and quiet. Gorgeous beach with chaises, etc. Big, wonderful heated pool. Tennis, which I used to fight for in WH but, here, you just walk on and play. The "studio" room I had was great. The kitchen even... More 

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long island
Senior Reviewer
6 reviews 6 reviews
6 hotel reviews
33 helpful votes 33 helpful votes
4 of 5 stars Reviewed September 20, 2014

My husband and I visit this beautiful slice of peace and heaven at least once a year-at the beginning of summer, before the Montauk craziness begins. We love the beach and the beach guys who set up our loungers, towels and umbrellas and we stay all day til the sun is going down--bliss. This hotel/timeshare is smaller than most of... More 

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ManagerWindward, General Manager at Windward Shores, responded to this review

Dear jamaicajc: I wish to express my gratitude for you taking the time to share such positive feedback on TripAdvisor following your stay with us! Windward Shores Ocean Resort is a slice of heaven indeed. We upgraded our landscaping last spring and our grounds are lovelier than ever. So that you know, we made a big push in renovating units... More 

Senior Reviewer
7 reviews 7 reviews
4 hotel reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed September 19, 2014 via mobile

I was referred to Windward Shores by another hotel that was sold out for the days that I wanted to vacation to Montauk. The property was beautifully landscaped, which I was unaware of from reviews I had read. I requested an updated room for the best price and was given a studio in the west building. It seemed like it... More 

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ManagerWindward, General Manager at Windward Shores, responded to this review

Dear Julia315845: It is always nice to hear of guests enjoying their time at Windward Shores Ocean Resort, and I thank you for your positive feedback. I am pleased to report that many of our units have been updated. We still have a few to do and will complete those this winter. We strive to offer excellent service and are... More 

Harding, NJ
Senior Reviewer
6 reviews 6 reviews
3 helpful votes 3 helpful votes
2 of 5 stars Reviewed September 14, 2014

As long as you stay outside, Windward Shores is a fine spot. The problem is interior. To say the 2 bedroom suite is dated is an understatement. There was peeling paint…missing molding, unpainted wood, where the molding was gone and blue painters tape along part of the flooring. The old, tired furniture looked like it as from an Austin Powers... More 

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ManagerWindward, General Manager at Windward Shores, responded to this review

Thank you for your review at tripadvisor. I only wish I could have had the opportunity to discuss your concerns while you were here. I passed your review information on to the owner of that unit. As Windward Shores is a resort co-op, all units are individually maintained and furnished. In the past two years, we have renovated and updated... More 

New York City, New York
Senior Reviewer
8 reviews 8 reviews
5 hotel reviews
6 helpful votes 6 helpful votes
3 of 5 stars Reviewed August 24, 2014

Booked a five night stay for the family in a studio. The beach is nice and the heated pool is too. The grounds are well taken care of and people working there are nice. BUT, 500$/night for a bare bones studio, is a bit much. Each room is owner owned and therefore some are renovated and some are not. Yet,... More 

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ManagerWindward, General Manager at Windward Shores, responded to this review

Thank you for your review at tripadvisor.com I only wish I could have had the opportunity to discuss your concerns while you were here. In the past two years, we have renovated and updated almost all of the units. I discussed your concerns with the owner and they have agreed to update their unit this fall. After reading your tripadvisor... More 

1 review
1 helpful vote 1 helpful vote
4 of 5 stars Reviewed July 23, 2014

If you are visiting Amagansett strictly for location, which we basically do, this is the perfect place for the family. The view from units 44,43 and 42 up top simply cannot be beat. Other top units are beach front but the dunes are in the way of ocean view, still a perfect location in my opinion. The units are large... More 

Was this review helpful? Yes 1
ManagerWindward, General Manager at Windward Shores, responded to this review

Thank you for your TripAdvisor review. The housekeeping effort here is tantamount to our success at Windward Shores, and I very much value your feedback. Please note that we had two housekeepers out sick for five days and while you were visiting us. Of course, that is not an excuse, but it is the truth. I am pleased to inform... More 

Akron, Ohio
2 reviews
2 helpful votes 2 helpful votes
1 of 5 stars Reviewed June 17, 2014

One of the worst "hotel properties" I have ever stayed in. I realize this was a "beach" property, but for $300 a night, it was ridiculous. I have stayed in better Motel 6 type properties. Many units are owned by individual investors who take better or worse care of their units. We stayed in unit 127 - avoid it. Front... More 

Was this review helpful? Yes 2
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Additional Information about Windward Shores

Address: 2062 Montauk Highway, Amagansett, NY 11930
Location: United States > New York > Long Island > Hamptons > Amagansett
Price Range (Based on Average Rates): $
Number of rooms: 46
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