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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
62° 20°
4
81° 26°
1
86° 33°
2
93° 29°
2
89° 19°
4
86° 32°
2
73° 20°
7
75° 15°
6
60° 8°
7
67° 6°
2
55° 3°
3
64° 16°
4
Apr
May
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Aug
Sep
Oct
Nov
Dec
Jan
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Mar
Rainy days

This climate histogram shows you the weather patterns in Southold. The warmest months in Southold are June and May, when temperatures reach 93 ˚F. The coolest month is November, when temperatures drop to 3 ˚F. The wettest month in Southold is March with 6.94 inches of rain, while the driest month is August with 1.2 inches of rain.

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What Expert Travelers Think

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  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

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  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

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