Southampton Vacation Rentals

Our Favorite Vacation Rentals in Southampton

  • Southampton Waterfront House
     Villa
    Booking.com
    From
    $1,060
  • Southampton Home w/Pool & Deck- 5 Minutes to Beach
     3br Home/Apartment
    HolidayLettings
    From
    $767
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • Hamptons Lofty Beach Barn - Pet Friendly
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $1,174
  • The Farm on the North Fork
     Country House
    Booking.com
    From
    $284
  • Southampton Water Front Retreat
     4br Cottage
    HolidayLettings
    From
    $1,855
  • Magnificent private Southampton Estate
     4br Home/Apartment
    HolidayLettings
    From
    $1,600
  • Amazing Hampton's Styled Getaway
     6br Home/Apartment
    HolidayLettings
    From
    $1,549

Check prices for these upcoming dates

Southampton Vacation Rentals with a Pool

  • Summer in the Hampton
    Good5br Home/Apartment
    Airbnb
    From
    $2,938
  • Charming Southampton Village Retreat
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,458
  • UNIQUE BEAUTIFUL FARMHOUSE * ROOM 3
    GoodHome/Apartment
    Airbnb
    From
    $367
  • SH Village 3BR w/Pool, Deck, BBQ
    Good4br Home/Apartment
    Airbnb
    From
    $1,239

Southampton Vacation Rentals with Wi-Fi

  • Stylish and Chic Southampton home
    Excellent2br Home/Apartment
    Airbnb
    From
    $630
  • 4 Bed, 2 Bath, Southampton, L.I.
    Excellent4br Home/Apartment
    Airbnb
    From
    $480
  • Southampton rental mins from beach!
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,601
  • Southampton Village-Available Year Round!
    Excellent3br Home/Apartment
    Airbnb
    From
    $537

Southampton Pet-Friendly Vacation Rentals

  • Great Rates in 2019- No Increases In Rates and Over Holiday Weeks
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $761
  • 5 Min to Bridgehampton n Sag Harbor 8 Min Ocean
     4br Home/Apartment
    HolidayLettings
    From
    $2,605
  • Hamptons Bay Home on Shinnecock Bay w/ Yard!
     2br Home/Apartment
    HolidayLettings
    From
    $372
  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641

Southampton New York City Travel Guide

Though the Hamptons is often considered as being the “go-to” summer break destination of choice for New Yorkers, Southampton New York is a pleasant alternative. Situated on the coastline of the Atlantic, the picturesque village of Southampton has a charming ambience and is filled with both history and affluence.

Things to Do in Southampton New York City

One of the best things to do in Southampton is to simply enjoy the chic atmosphere of the town itself. Main Street is the area’s main promenade and is lined with boutique stores, antique sellers and sophisticated places to enjoy dinner or an evening tipple. Those interested can catch a polo match at the nearby equestrian club. It is also worth taking a drive or a stroll through the “Estate” area of Southampton where some of the grandest mansions are located.

Best Time to Visit Southampton New York City

The best time to visit Southampton is during the summer months.

Price and Availability in Southampton

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Southampton tends to be Sunday, while the most expensive day tends to be Friday. Vacation homes in Southampton 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 Southampton is in June, while the cheapest month is in January. The most popular time to book a vacation rental in Southampton is in the high season in August. Southampton has its low season in November, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Southampton

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

What Expert Travelers Think

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    My Anasa
    My AnasaMy Anasa
  • — 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
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

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