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Southold Vacation Rentals

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Our Favorite Vacation Rentals in Southold

  • Five Bedroom Italianate Great House - The Gem of East Marion
    Five Bedroom Italianate Great House - The Gem of East Marion
    Excellent5br Home/Apartment
    HolidayLettingsFrom $1660
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  • holiday home for max. 8 persons in Water Mill, NewYork
    holiday home for max. 8 persons in Water Mill, NewYork
     Country House
    TUIVillasFrom $7820
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  • Victorian Seasons 1 bedroom Carriage House Duplex
    Victorian Seasons 1 bedroom Carriage House Duplex
    Excellent1br Home/Apartment
    HolidayLettingsFrom $487
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  • holiday home for max. 14 persons in Southampton, NewYork
    holiday home for max. 14 persons in Southampton, NewYork
     Country House
    TUIVillasFrom $50606
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  • Cottage in the historic district
    Cottage in the historic district
    Excellent2br Home/Apartment
    HolidayLettingsFrom $2061
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  • holiday home for max. 12 persons in East Hampton, NewYork
    holiday home for max. 12 persons in East Hampton, NewYork
     Country House
    TUIVillasFrom $15358
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  • North Fork Loft - Perfect for Wine & Food Weekends
    North Fork Loft - Perfect for Wine & Food Weekends
     5br Home/Apartment
    HolidayLettingsFrom $1082
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  • holiday home for max. 16 persons in Bridgehampton, NewYork
    holiday home for max. 16 persons in Bridgehampton, NewYork
     Country House
    TUIVillasFrom $44014
    View Deal
See all 245 deals in Southold

Southold Vacation Rentals with a Pool

  • Water View First Floor Condo
    Water View First Floor Condo
    Good2br Home/Apartment
    AirbnbFrom $699
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  • Sag Harbor Quiet Retreat Steps from the Bay
    Sag Harbor Quiet Retreat Steps from the Bay
    Excellent1br Home/Apartment
    AirbnbFrom $723
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  • Spacious Ranch-4 acres. Near Wineries & Greenport
    Spacious Ranch-4 acres. Near Wineries & Greenport
    Excellent4br Home/Apartment
    AirbnbFrom $1808
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  • Retro Yacht - NoFo Winetasting
    Retro Yacht - NoFo Winetasting
    Excellent2br Home/Apartment
    AirbnbFrom $576
    View Deal
See all deals in Southold with a pool

Southold Vacation Rentals with Wi-Fi

  • Beachwood Manor
    Beachwood Manor
    Good3br Home/Apartment
    AirbnbFrom $622
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  • Historical Home near GREENPORT, walk to wineries.
    Historical Home near GREENPORT, walk to wineries.
     6br Home/Apartment
    AirbnbFrom $1065
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  • The Lord Shipyard Mansion & Estate
    The Lord Shipyard Mansion & Estate
     5br Home/Apartment
    AirbnbFrom $2797
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  • the old brick storefront
    the old brick storefront
     1br Home/Apartment
    AirbnbFrom $410
    View Deal
See all deals in Southold with WiFis

Southold Pet-Friendly Vacation Rentals

  • Cozy North Fork weekend getaway
    Cozy North Fork weekend getaway
     3br Home/Apartment
    AirbnbFrom $593
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  • Shelter Island Getaway
    Shelter Island Getaway
    Good3br Island
    AirbnbFrom $1017
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  • Shelter Island get away
    Shelter Island get away
    Excellent3br Home/Apartment
    AirbnbFrom $664
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  • Rustic barn with cushy amenities
    Rustic barn with cushy amenities
    Good2br Farmhouse
    AirbnbFrom $452
    View Deal
See all deals in Southold that allow pets

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

Most expensive
Most availability
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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 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 Weather in Southold

96º 45º
2.67
91º 47º
6.51
90º 44º
4.71
77º 14º
6.29
66º 12º
8.77
60º 12º
5.41
55º -3º
2.64
60º 3º
5.15
60º 16º
5.18
68º 18º
3.6
81º 34º
2.63
89º 37º
1.93
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
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 January, when temperatures drop to -3 ˚F. The wettest month in Southold is November with 8.77 inches of rain, while the driest month is June with 1.93 inches of rain.

What Expert Travelers Think

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