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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.

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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.
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The Weather in Southold

Rainy days
83° 43°
5
77° 33°
6
68° 15°
2
60° 16°
1
53° 7°
2
54° 5°
3
72° 15°
3
72° 19°
4
89° 31°
4
87° 40°
1
90° 47°
5
92° 52°
4
Sep
Oct
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Jan
Feb
Mar
Apr
May
Jun
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Aug
Rainy days

This climate histogram shows you the weather patterns in Southold. The warmest months in Southold are May and June, when temperatures reach 92 ˚F. The coolest month is November, when temperatures drop to 5 ˚F. The wettest month in Southold is March with 6.05 inches of rain, while the driest month is July with 1.19 inches of rain.

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What Expert Travelers Think

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    Whitney Wear
    Whitney WearTravel Better Guide
    Travel Better Guide

  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
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  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae
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