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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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Watermill things to do

 

Wolffer Estate Vineyard

You may find yourself feeling unwelcome. If it wasn't for how stunning this place is, I would have only given it 3 stars. The service was unfortunately...read more

 

Cooper's Beach

This beach is pretty much the same as all the beaches in the hamptons except that it's more crowded. Most people don't like crowded beaches, but I actually...read more

 

Duckwalk Vineyards

I came here with a group of my friends as part of a birthday celebration in the hamptons. Even though it was a large group and they initially told us we...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

 

Mattebella Vineyards

We stopped here to celebrate after my fiance proposed to me at Lavender by the Bay in East Marion last weekend. This was our last wine tasting stop of the...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

 

Raphael Vineyard and Winery

Raphael Vineyards is a beautiful location to visit. The inside is grand with huge chandeliers and a wonderful circle bar in the middle as the focal point....read more

 

Sannino's Bella Vita Vineyard

Small winery, not crowded, it gives intimate feel. The staffs are very friendly, personable & knowledge. I had a great time chatting with them. The grape...read more

 

Croteaux Vineyards

This was my first foray into LI vineyard wine tasting and this was a great first stop. They don't allow commercial buses to drop off to the overall vibe is...read more

 

Coffee Pot Cellars

GEWURZTRAMINER! One of their whites. It's incredibly floral and fragrant. And since I have a thing for the floral scent, I am glad I stopped by. Everything...read more

 

Pindar Vineyards

Stop here yesterday with my girlfriends after a long day exploring the north fork. I thought at first we were at the wrong place... the outside of the...read more

 

Sparkling Pointe

Not at all intimate. Think overly giddy "brides maids showing up in club wear & arriving in white limos" argh. Or an enterage of "Housewives of some NYC...read more

 

One Woman Wines & Vineyard

I've been ruminating over my experience here. Quite yet powerful. Intimate but serious. Precise yet easy going. Gabrielle, daughter to the proprietor, over...read more

 

The Lenz Winery

This is a classic Long Island winery that offers something truly unique to the area - some world class wines! Our group was greeted enthusiastically, and...read more

 

The Winemaker Studio

One of those "hidden gems" in the North Fork. Each time I get to stop by, I am thoroughly impressed. They offer wines from various winemakers and also...read more

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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 - $714 /nt
    $9,000 - $16,000 /mth
 
 
 
 
 

6 reviews write a review

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
    $7,500 /wk
 
 
 
 
 

15 reviews write a review

Hamptons architect designed Home for 2 week stays in Fall
Watermill House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $214 - $357 /nt
 
 
 
 
 

13 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 - $3,500 /nt
    $90,000 /mth
 
 
 
 
 

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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) $10,000 - $36,167 /mth
 
 
 
 
 

6 reviews write a review

Private Southampton Getaway W/3 Master Suites, 6,000sf!
Watermill House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 4
  • rates (USD) $30,000 /mth
 
 
 
 
 

2 reviews write a review

Lovely Hamptons Rental
Watermill House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $2,333 - $4,200 /wk
 
 
 
 
 

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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

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
 
 
 
 
 

1 reviews write a review

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

Grand SH Luxury Estate - 90 acre reserve -Heated Pool & Tennis!!!!!
Watermill House Rental Picture
  • bedrooms 10
  • rental type House
  • sleeps 30
  • baths 10
  • rates (USD) $2,000 - $8,500 /nt
    $7,500 - $18,000 /wk
 
 
 
 
 

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