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Southold Vacation Rentals

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Our Favorite Vacation Rentals in Southold

  • The Farm on the North Fork
     Country House
    Booking.com
    From
    $305
  • Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,574
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • Relaxed Village Farmhouse
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $702
  • Downtown Greenport Apt w/Porch Near Shelter Island
     Home/Apartment
    HolidayLettings
    From
    $296
  • Five Bedroom Italianate Great House - The Gem of East Marion
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,660
  • Beautiful French Country Cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $615
  • East Marion Home Walk to Beach-3 Mi to Greenport!
     3br Home/Apartment
    HolidayLettings
    From
    $419
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Check prices for these upcoming dates

Southold Vacation Rentals with a Pool

  • Serene and private North Fork home w/pool
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,045
  • Fabulous beach house , Pool, hot tub, outdoor shwr
    Good4br Home/Apartment
    Airbnb
    From
    $994
  • Waterfront carriage house studio
    ExcellentHome/Apartment
    Airbnb
    From
    $410
  • Secluded and Sheltered
    Excellent4br Home/Apartment
    Airbnb
    From
    $336
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Southold Vacation Rentals with Wi-Fi

  • Sweet Southold Charmer
    Excellent2br Home/Apartment
    Airbnb
    From
    $412
  • Beach house @ NoFo
    Excellent3br Home/Apartment
    Airbnb
    From
    $942
  • Cottage on the Great Pond
    Excellent2br Home/Apartment
    Airbnb
    From
    $271
  • New home across from the water!
    Excellent4br Home/Apartment
    Airbnb
    From
    $494
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Southold Pet-Friendly Vacation Rentals

  • Sag Harbor Perfect For Extended Family and Friends
     5br Home/Apartment
    HolidayLettings
    From
    $3,075
  • 5 Min to Bridgehampton n Sag Harbor 8 Min Ocean
     4br Home/Apartment
    HolidayLettings
    From
    $3,026
  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641
  • Amazing Hampton's Styled Getaway
     6br Home/Apartment
    HolidayLettings
    From
    $2,221
Show all

Southold, New York Travel Guide

Southold is one of the oldest towns in New York State. Today, its wineries, restaurants, and untouched nature make it a perfect place for a calm, low-key getaway.

Things to Do in Southold, New York

Top things to do include wine tasting at Pindar Vineyards, lavender picking at Lavender By the Bay, and relaxing among marine wildlife and woods at Orient Beach State Park.

Best Time to Visit Southold, New York

The best time to visit Southold is from mid June to late September.

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Price and Availability in Southold

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Southold tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Southold 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 Southold is in August, while the cheapest month is in October. The most popular time to book a vacation rental in Southold is in the high season in August. Southold has its low season in February, when less people are visiting and the vacation home occupancy rate drops.
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The Weather in Southold

Rainy days
88° 2°
5
88° -3°
3
63° 5°
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 Southold. The hottest month in Southold is March, when temperatures peak at 129 ˚F. The coolest month is November, when temperatures drop to -3 ˚F. The wettest month in Southold is January with 7.02 inches of rain, while the driest month is April with 1.1 inches of rain.

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What Expert Travelers Think

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    Clwyd ProbertWhitehat
    Visit Whitehat

  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

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    JazThe Life of a Social Butterfly
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