Watermill Vacation Rentals

Our Favorite Vacation Rentals in Watermill

  • Southampton Waterfront House
     Villa
    Booking.com
    From
    $1,060
  • Hamptons Lofty Beach Barn - Pet Friendly
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $1,174
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • Amazing Hampton's Styled Getaway
     6br Home/Apartment
    HolidayLettings
    From
    $1,549
  • Southampton Home w/Pool & Deck- 5 Minutes to Beach
     3br Home/Apartment
    HolidayLettings
    From
    $767
  • SOUTHAMPTON POOL & TENNIS
     5br Home/Apartment
    HolidayLettings
    From
    $1,489
  • 5 Min to Bridgehampton n Sag Harbor 8 Min Ocean
     4br Home/Apartment
    HolidayLettings
    From
    $2,605
  • Beautiful Bridgehampton Home
     5br Home/Apartment
    HolidayLettings
    From
    $2,147

Check prices for these upcoming dates

Watermill Vacation Rentals with a Pool

  • Lofty Beach Barn
    Excellent4br Home/Apartment
    Airbnb
    From
    $819
  • Modern House working fireplace close to the beach
    Excellent3br Home/Apartment
    Airbnb
    From
    $720
  • Pristine home in Water Mill
     4br Home/Apartment
    Airbnb
    From
    $1,271
  • Magical Hamptons 4 Beds/4 baths Pool
    Good4br Home/Apartment
    Airbnb
    From
    $986

Watermill Vacation Rentals with Wi-Fi

  • Elegant Modern Artist's Residence
    Excellent2br Home/Apartment
    Airbnb
    From
    $390
  • Serene Bridgehampton Garden Cottage: walk to Beach
    Excellent3br Home/Apartment
    Airbnb
    From
    $383
  • Summer fun or an off-season adventure? Enjoy both!
    Excellent3br Home/Apartment
    Airbnb
    From
    $367
  • watermill, oversized beach cottage,
    Excellent5br Cottage
    Airbnb
    From
    $2,825

Watermill Pet-Friendly Vacation Rentals

  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641
  • Luxury East Hampton Home w/Private Saltwater Pool!
     5br Home/Apartment
    HolidayLettings
    From
    $1,293
  • Great Rates in 2019- No Increases In Rates and Over Holiday Weeks
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $761
  • NEW! East Hampton Family Getaway ~2.5 Mi to Beach!
     3br Home/Apartment
    HolidayLettings
    From
    $672

Water Mill, New York Travel Guide

Situated on the East End of Long Island, Water Mill is a Southampton hamlet with both a functional water mill and windmill -- rare features that make it unique compared to any other East End town. Once an overlooked town off Route 27, Water Mill is now a lively place for weekenders indulge in a secret paradise.

Things to Do in Water Mill, New York

Top attractions include the beautiful Parrish Art Museum, Hank's Pumpkin Town, and apple picking at Seven Ponds Orchard and Milk Pail U-Pick Farm.

Best Places to Stay in Water Mill, New York

For a classic Hamptons experience, stay at an inn or a bed and breakfast.

Best Time to Visit Water Mill, New York

The best time to visit is around April to June and September to early November, when the weather is warm and crowds are small.

Food in Water Mill, New York

The best places to eat are Calissa for upscale Greek fare at a beach hideaway, Suki Zuki for good Japanese food, and Bistro Ete for a casual French meal.

Price and Availability in Watermill

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Watermill tends to be Sunday, while the most expensive day tends to be Friday. Vacation homes in Watermill tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Watermill is in October, while the cheapest month is in April. The most popular time to book a vacation rental in Watermill is in the high season in August. Watermill has its low season in February, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Watermill

Rainy days
88°
5
88° -3°
3
63°
3
99° 10°
7
84° 35°
5
90° 35°
3
97° 53°
3
88° 47°
2
80° 35°
1
129° 30°
6
69° 13°
3
58° 10°
7
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Watermill. The warmest months in Watermill are March and September, when temperatures reach 129 ˚F. The coolest month is November, when temperatures drop to -3 ˚F. The wettest month in Watermill is January with 7.02 inches of rain, while the driest month is April with 1.1 inches of rain.

What Expert Travelers Think

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

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