Southold Vacation Rentals

Our Favorite Vacation Rentals in Southold

  • The Farm on the North Fork
     Country House
    Booking.com
    From
    $305
  • Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,574
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • Relaxed Village Farmhouse
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $702
  • Downtown Greenport Apt w/Porch Near Shelter Island
     Home/Apartment
    HolidayLettings
    From
    $296
  • Five Bedroom Italianate Great House - The Gem of East Marion
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,660
  • Beautiful French Country Cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $615
  • East Marion Home Walk to Beach-3 Mi to Greenport!
     3br Home/Apartment
    HolidayLettings
    From
    $419

Check prices for these upcoming dates

Southold Vacation Rentals with a Pool

  • Serene and private North Fork home w/pool
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,045
  • Fabulous beach house , Pool, hot tub, outdoor shwr
    Good4br Home/Apartment
    Airbnb
    From
    $994
  • Waterfront carriage house studio
    ExcellentHome/Apartment
    Airbnb
    From
    $410
  • Secluded and Sheltered
    Excellent4br Home/Apartment
    Airbnb
    From
    $336

Southold Vacation Rentals with Wi-Fi

  • Sweet Southold Charmer
    Excellent2br Home/Apartment
    Airbnb
    From
    $412
  • Beach house @ NoFo
    Excellent3br Home/Apartment
    Airbnb
    From
    $942
  • Cottage on the Great Pond
    Excellent2br Home/Apartment
    Airbnb
    From
    $271
  • New home across from the water!
    Excellent4br Home/Apartment
    Airbnb
    From
    $494

Southold Pet-Friendly Vacation Rentals

  • Sag Harbor Perfect For Extended Family and Friends
     5br Home/Apartment
    HolidayLettings
    From
    $3,075
  • 5 Min to Bridgehampton n Sag Harbor 8 Min Ocean
     4br Home/Apartment
    HolidayLettings
    From
    $3,026
  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641
  • Amazing Hampton's Styled Getaway
     6br Home/Apartment
    HolidayLettings
    From
    $2,221

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
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
88°
5
88° -3°
3
63°
3
99° 10°
7
84° 35°
5
90° 35°
3
97° 53°
3
88° 47°
2
80° 35°
1
129° 30°
6
69° 13°
3
58° 10°
7
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
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

  • — 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 travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly

Destinations near Southold

  • New York14,524 Properties
  • Brooklyn9,352 Properties
  • Niagara Falls3,942 Properties
  • Queens2,643 Properties
  • Lake Placid1,424 Properties
  • Montauk1,415 Properties
  • Ithaca1,381 Properties
  • Sag Harbor805 Properties
  • Rochester794 Properties
  • Amagansett764 Properties
  • Lake George Village762 Properties
  • Hampton Bays669 Properties
  • Southampton662 Properties
  • Springs645 Properties
  • Ellicottville590 Properties
  • Albany552 Properties
  • Hunter550 Properties
  • Hudson541 Properties
  • Village of East Hampton526 Properties
  • Saugerties517 Properties
  • Woodstock511 Properties
  • Windham478 Properties
  • Cooperstown475 Properties
  • Ocean Beach430 Properties
  • Canandaigua423 Properties
  • Lake George419 Properties
  • Geneva407 Properties
  • Bridgehampton394 Properties
  • Saranac Lake392 Properties
  • Beacon367 Properties
  • Kingston357 Properties
  • Penn Yan348 Properties
  • Wilmington344 Properties
  • Hammondsport337 Properties
  • Watkins Glen332 Properties
  • Cherry Grove330 Properties
  • Noyack330 Properties
  • Syracuse320 Properties
  • Staten Island319 Properties
  • Buffalo304 Properties
  • Yonkers301 Properties
  • Watermill301 Properties
  • Chestertown287 Properties
  • Alexandria Bay284 Properties
  • New Paltz278 Properties
  • Greenport272 Properties
  • East Quogue272 Properties
  • Bolton Landing250 Properties
  • Long Beach245 Properties
  • Chautauqua242 Properties
  • Warrensburg240 Properties
  • Wainscott239 Properties
  • Queensbury232 Properties
  • Cortland231 Properties
  • North Creek229 Properties
  • Old Forge229 Properties
  • Binghamton221 Properties
  • Plattsburgh216 Properties
  • Shelter Island215 Properties
  • White Plains215 Properties
  • Auburn214 Properties
  • Rhinebeck211 Properties
  • Catskill211 Properties
  • Westhampton Beach202 Properties
  • Westhampton199 Properties
  • Poughkeepsie195 Properties
  • Trumansburg195 Properties
  • Pulaski194 Properties
  • Skaneateles191 Properties
  • Saratoga Springs182 Properties
  • Schroon Lake163 Properties
  • Dundee160 Properties
  • Clayton152 Properties
  • Amherst150 Properties
  • Quogue145 Properties
  • Newburgh133 Properties
  • Mount Vernon116 Properties
  • Fire Island116 Properties
  • Tupper Lake102 Properties
  • Diamond Point91 Properties
  • Fishkill88 Properties
  • Fleischmanns86 Properties
  • Millbrook61 Properties
  • Riverhead58 Properties
  • Ellenville57 Properties
  • Chatham55 Properties
  • City of Gloversville51 Properties
  • Port Jefferson39 Properties
  • Croton-on-Hudson36 Properties
  • Findley Lake34 Properties
  • Adirondack32 Properties
  • Sodus Point29 Properties
  • Washingtonville19 Properties
  • Star Lake8 Properties