Southold Vacation Rentals

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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.

Price and Availability in Southold

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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.

The Weather in Southold

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

What Expert Travelers Think

  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa

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