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Windward Shores

2062 Montauk Highway, Amagansett, NY 11930
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Best prices for: 1 room 1 guest
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Windward Shores
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Windward Shores
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44 reviews from our community

Traveler rating
    18
    13
    8
    2
    3
See reviews for
11
16
Solo
0
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
Traveler tips help you choose the right room.   Room tips (14)
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    (44)
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Reviewer
4 reviews 4 reviews
5 of 5 stars Reviewed January 9, 2015

loved this !! we had the studio room, perfect just for the 2 of us. renovated and with a full kitchen which was great for us to cook since not too much is open this time of year. We stayed NYE till the coming up Sunday. The front desk was super sweet and accommodated us. The beach is literally in... More 

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Selden, New York
Senior Contributor
27 reviews 27 reviews
5 hotel reviews
7 helpful votes 7 helpful votes
4 of 5 stars Reviewed January 6, 2015

Recently stayed here for my fiance's birthday. We had a friend staying with us so we ended up renting a 2 bedroom ocean view corner unit, walk to boardwalk,beach .Had great spiral staircase leading to loft. Small kitchen as well as two bathroom and 2 additional beds in the loft. Had a nice little patio area outside the living room,... More 

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Bronx, New York
Top Contributor
114 reviews 114 reviews
9 hotel reviews
29 helpful votes 29 helpful votes
4 of 5 stars Reviewed December 3, 2014

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
3 helpful votes 3 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 

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2 reviews
5 of 5 stars Reviewed September 30, 2014

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
7 reviews 7 reviews
7 hotel reviews
36 helpful votes 36 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 Contributor
22 reviews 22 reviews
6 hotel reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed September 19, 2014

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 

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