AllTheRooms.

Southold Vacation Rentals

  1. Vacation Rental Search
  2. United States of America
  3. New York
  4. Southold

Check prices for these upcoming dates

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.

More+

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.
More+

The Weather in Southold

Rainy days
67° 6°
2
55° 3°
3
64° 16°
4
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
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 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.

More+

What Expert Travelers Think

  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
    Visit Alli Sims

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
    Middle Class Dad

  • — 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
    Sarah PoolTammymum
    Visit Tammymum

Destinations near Southold

  • New York14,756 Properties
  • Brooklyn9,498 Properties
  • Niagara Falls4,147 Properties
  • Queens2,688 Properties
  • Montauk1,493 Properties
  • Lake Placid1,461 Properties
  • Ithaca1,445 Properties
  • Sag Harbor842 Properties
  • Rochester811 Properties
  • Amagansett793 Properties
  • Lake George Village769 Properties
  • Hampton Bays712 Properties
  • Springs700 Properties
  • Southampton699 Properties
  • Ellicottville682 Properties
  • Albany592 Properties
  • Hunter585 Properties
  • Hudson561 Properties
  • Village of East Hampton543 Properties
  • Saugerties542 Properties
  • Woodstock520 Properties
  • Cooperstown510 Properties
  • Windham504 Properties
  • Chautauqua476 Properties
  • Lake George462 Properties
  • Ocean Beach450 Properties
  • Canandaigua443 Properties
  • Geneva433 Properties
  • Bridgehampton419 Properties
  • Saranac Lake403 Properties
  • Penn Yan382 Properties
  • Beacon380 Properties
  • Kingston370 Properties
  • Hammondsport357 Properties
  • Wilmington352 Properties
  • Noyack349 Properties
  • Cherry Grove338 Properties
  • Watkins Glen337 Properties
  • Yonkers332 Properties
  • Staten Island331 Properties
  • Syracuse329 Properties
  • Watermill318 Properties
  • Buffalo306 Properties
  • Chestertown296 Properties
  • New Paltz294 Properties
  • East Quogue291 Properties
  • Alexandria Bay287 Properties
  • Greenport285 Properties
  • Long Beach265 Properties
  • Queensbury265 Properties
  • Bolton Landing265 Properties
  • Warrensburg255 Properties
  • Wainscott246 Properties
  • Old Forge243 Properties
  • North Creek242 Properties
  • Cortland233 Properties
  • Shelter Island228 Properties
  • Binghamton227 Properties
  • Plattsburgh224 Properties
  • Catskill222 Properties
  • White Plains222 Properties
  • Auburn222 Properties
  • Rhinebeck220 Properties
  • Westhampton218 Properties
  • Westhampton Beach215 Properties
  • Poughkeepsie211 Properties
  • Skaneateles206 Properties
  • Trumansburg205 Properties
  • Pulaski198 Properties
  • Saratoga Springs195 Properties
  • Amherst183 Properties
  • Dundee171 Properties
  • Clayton165 Properties
  • Schroon Lake164 Properties
  • Quogue157 Properties
  • Newburgh141 Properties
  • Mount Vernon124 Properties
  • Fire Island119 Properties
  • Tupper Lake107 Properties
  • Diamond Point98 Properties
  • Fleischmanns91 Properties
  • Fishkill90 Properties
  • Millbrook67 Properties
  • Riverhead60 Properties
  • Ellenville59 Properties
  • Chatham56 Properties
  • City of Gloversville53 Properties
  • Port Jefferson40 Properties
  • Croton-on-Hudson38 Properties
  • Findley Lake38 Properties
  • Adirondack33 Properties
  • Sodus Point31 Properties
  • Washingtonville20 Properties
  • Star Lake11 Properties