Southold Vacation Rentals

Our Favorite Vacation Rentals in Southold

  • Victorian Seasons 5-bedroom Manor
     Country House
    Booking.com
    From
    $1,250
  • Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,345
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • Downtown Greenport Apt w/Porch Near Shelter Island
     Home/Apartment
    HolidayLettings
    From
    $290
  • Sag Harbor Great Loc + Pool
     Country House
    Booking.com
    From
    $475
  • Beautiful French Country Cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $573
  • Sag Harbor Privacy 6Min Bridgehampton
     Country House
    Booking.com
    From
    $475
  • East Marion Home Walk to Beach-3 Mi to Greenport!
     3br Home/Apartment
    HolidayLettings
    From
    $436

Check prices for these upcoming dates

Southold Vacation Rentals with a Pool

  • Fabulous beach house , Pool, hot tub, outdoor shwr
    Excellent4br Home/Apartment
    Airbnb
    From
    $994
  • Serene and private North Fork home w/pool
    Excellent4br Home/Apartment
    Airbnb
    From
    $932
  • Waterfront carriage house studio
    ExcellentHome/Apartment
    Airbnb
    From
    $410
  • Cliffside Resort! Greenport 2br/2ba Beach Poolside
    Excellent2br Home/Apartment
    Airbnb
    From
    $324

Southold Vacation Rentals with Wi-Fi

  • Cozy Barn Loft Apartment on the NOFO Wine Trail
    ExcellentHome/Apartment
    Airbnb
    From
    $339
  • Unique farmhouse in village
    Excellent3br Home/Apartment
    Airbnb
    From
    $452
  • Captain's Cove
     2br Home/Apartment
    Airbnb
    From
    $424
  • Cottage on the Great Pond
    Excellent2br Home/Apartment
    Airbnb
    From
    $271

Southold Pet-Friendly Vacation Rentals

  • Amazing Hampton's Styled Getaway
     6br Home/Apartment
    HolidayLettings
    From
    $876
  • Hamptons Lofty Beach Barn - Pet Friendly
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $1,288
  • Sag Harbor Perfect For Extended Family and Friends
     5br Home/Apartment
    HolidayLettings
    From
    $1,946
  • Sag Harbor Waterfront Dock, Pool Kayak & Paddleboards Aug10-17 & Labor Day avil
     8br Home/Apartment
    HolidayLettings
    From
    $2,376

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 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 º44
5
77 º14
6
66 º12
9
60 º12
5
55 º-3
3
60 º3
5
60 º16
5
68 º18
4
81 º34
3
89 º37
2
96 º45
3
91 º47
7
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Southold. The warmest months in Southold are June and May, when temperatures reach 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.

What Expert Travelers Think

  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

    Monica
    MonicaNYCTechMommy
  • — 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.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — 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!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker

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