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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
    $223
  • Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,345
  • Victorian Seasons 5-bedroom Manor
     Country House
    Booking.com
    From
    $1,250
  • Relaxed Village Farmhouse
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $643
  • Victorian Seasons Cape
     Country House
    Booking.com
    From
    $650
  • East Marion Home Walk to Beach-3 Mi to Greenport!
     3br Home/Apartment
    HolidayLettings
    From
    $442
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • SOUTHAMPTON POOL & TENNIS
     5br Home/Apartment
    HolidayLettings
    From
    $1,489
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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
    $932
  • Fabulous beach house , Pool, hot tub, outdoor shwr
    Good4br Home/Apartment
    Airbnb
    From
    $994
  • Waterfront carriage house studio
    ExcellentHome/Apartment
    Airbnb
    From
    $325
  • Waterfront Condo C-204 at The Cliffside Resort
    Excellent2br Home/Apartment
    Airbnb
    From
    $466
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Southold Vacation Rentals with Wi-Fi

  • Sweet Southold Charmer
    Excellent2br Home/Apartment
    Airbnb
    From
    $480
  • Beach house @ NoFo
    Excellent3br Home/Apartment
    Airbnb
    From
    $942
  • Unique farmhouse in village
    Good3br Home/Apartment
    Airbnb
    From
    $452
  • Cottage on the Great Pond
    Excellent2br Home/Apartment
    Airbnb
    From
    $271
Show all

Southold Pet-Friendly Vacation Rentals

  • 5 Min to Bridgehampton n Sag Harbor 8 Min Ocean
     4br Home/Apartment
    HolidayLettings
    From
    $2,605
  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641
  • Amazing Hampton's Styled Getaway
     6br Home/Apartment
    HolidayLettings
    From
    $1,549
  • Hamptons Lofty Beach Barn - Pet Friendly
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $1,174
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
66° 12°
9
60° 12°
5
55° -3°
3
60° 3°
5
60° 16°
5
68° 18°
4
81° 34°
3
89° 37°
2
96° 45°
3
91° 47°
7
90° 44°
5
77° 14°
6
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Southold. The hottest month in Southold is June, when temperatures peak at 96 ˚F. The coolest month is December, when temperatures drop to -3 ˚F. The wettest month in Southold is February with 8.77 inches of rain, while the driest month is July with 1.93 inches of rain.

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What Expert Travelers Think

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  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

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