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Vacation Rentals in Watermill, New York

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Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Watermill, New York vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Watermill are added and updated every week!

Compared to hotels, Watermill vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Watermill, New York Vacation Rentals and Tourism

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Wolffer Estate Vineyard

This was my first wine tasting at a vineyard and it was the perfect outing for a not so great beach day. I was told that they are "different from other...read more

 

Wolffer Estate

Beautiful vineyard, romantic tasting room. Overlooking vineyard outdoor porch for relaxing afternoon for tasting wines. It was Friday afternoon, winery was...read more

 

Cooper's Beach

This is my favorite beach on the North East Coast for sunning . . . for surfing though, I would go to Montauk, particularly Ditch Plains which is a point...read more

 

Duckwalk Vineyards

Came by Duckwalk this afternoon for the wine tasting, and I've gotta say: my wife and I were pleasantly surprised! Mike took really good care of us - he's...read more

 

Sparkling Pointe

Sparlking Pointe is more or less an outlier in LI's wine region. They only do one thing - the bubbly. Like many of LI's wineries, it certainly is...read more

 

Raphael Vineyard and Winery

Raphael Winery is hands down my favorite on the North Fork! We have gone there several times and we are never disappointed. The wines are delicious and it...read more

 

Cedar Point County Park

Camping ranked very high on the list of things I had absolutely no interest in doing, ever. Here's why: - Setup and break down is too much damn work....read more

 

Channing Daughters Winery

Love this place. First the wine: it's terrific. Easily the best on the South Fork, and far beyond that. It's really well thought out, and extremely...read more

 

Pindar Vineyards

As someone who has been a wine enthusiast for years, I can confidently say that this was the worst wine I have ever had in my life. Worse than Barefoot, or...read more

 

Croteaux Vineyards

It's like walking onto the set of a movie. Suddenly I feel like I'm in a scene from under the tuscan sun and it's pretty amazing. They don't allow the mega...read more

 

Sannino's Bella Vita Vineyard

This was the second stop on our wine tour and we opted to have the Vine to Wine tour, which includes about 5 tastings and taught us all about the wine...read more

 

Mattebella Vineyards

Yay for you for finding this review! It means you will know about a hidden gem on the North Fork - Mattebella! Have been going here for years (after...read more

 

One Woman Wines & Vineyard

By far our FAVORITE stop of the day. We had a great time talking to the people behind the counter. Can't wait to enjoy the wines we brought home from here.read more

 

The Lenz Winery

We were here for about an hour while on a wine tour that hit up 3 vineyards. We arrived late so we didn't get to do anything other than sample 4 wines in...read more

 

Duck Walk Vineyards

The place is clean which is what made the review 3 stars. I wish I could even rate it a 2.5. They didn't have our reservation written down, but accommodated...read more

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The Ultimate Luxury Estate Rental in The Hamptons
Watermill Estate Rental Picture
  • bedrooms 10
  • rental type Estate
  • owner badgeowner badge
  • sleeps 40
  • baths 17
  • rates (USD) $7,500 /nt
 
 
 
 
 

5 reviews write a review

The Ultimate Luxury Estate Rental in The Hamptons
Watermill Estate Rental Picture
  • bedrooms 10
  • rental type Estate
  • owner badgeowner badge
  • sleeps 40
  • baths 17½
  • rates (USD) $7,500 /nt
 
 
 
 
 

4 reviews write a review

Best Views in the Hamptons. Wake up to Horses..
Watermill House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $286 - $1,167 /nt
    $1,600 /wk
    $4,000 - $36,167 /mth
 
 
 
 
 

6 reviews write a review

2014 Long Term rental in HAMPTONS Solar Home, pool & Playground
Watermill House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $357 - $3,000 /nt
    $3,750 - $6,500 /wk
    $8,000 - $27,500 /mth
 
 
 
 
 

11 reviews write a review

LUXURY 4 BEDROOM HOUSE MINUTES TO EVERYTHING! NEW 25 X 50 SALT GENERATED POOL!
Watermill Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $429 - $750 /nt
    $5,000 /wk
    $9,000 - $16,000 /mth
 
 
 
 
 

6 reviews write a review

Lovely Hamptons Rental
Watermill House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $286 /nt
 
 
 
 
 

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Beautiful, Pristine and Private Country House with Designer Pool & Spa
Watermill Farmhouse Rental Picture
  • bedrooms 4
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $286 - $1,071 /nt
    $7,000 - $7,500 /wk
 
 
 
 
 

10 reviews write a review

Architectural Digest Cover Home in the Hamptons
Watermill Lodge Rental Picture
  • bedrooms 4
  • rental type Lodge
  • sleeps 8
  • baths 6
  • rates (USD) $1,500 - $3,000 /nt
 
 
 
 
 

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The Water Mill Hideaway - Walk To Town! - Now Booking For 2014!
Watermill House Rental Picture
  • bedrooms 8
  • rental type House
  • sleeps 18
  • baths
  • rates (USD) $1,000 /nt
 
 
 
 
 

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Spring or Summer Hampton's Rental with Pool and Tennis
Watermill House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $3,500 /wk
 
 
 
 
 

2 reviews write a review