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Southold Vacation Rentals

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Our Favorite Vacation Rentals in Southold

  • holiday home for max. 6 persons in Southampton, NewYork
    holiday home for max. 6 persons in Southampton, NewYork
     
    TUIVillasFrom $3805
    View Deal
  • Sunny Room in Sag Harbor
    Sunny Room in Sag Harbor
     
    Booking.comFrom $300
    View Deal
  • Beautiful Luxury Home with Pool in the Heart of Wine Country
    Beautiful Luxury Home with Pool in the Heart of Wine Country
     
    HolidayLettingsFrom $1231
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  • Topping Rose House
    Topping Rose House
     
    NextTripFrom $1751
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  • holiday home for max. 8 persons in Water Mill, NewYork
    holiday home for max. 8 persons in Water Mill, NewYork
     
    TUIVillasFrom $6376
    View Deal
  • Sag Harbor Privacy 6Min Bridgehampton
    Sag Harbor Privacy 6Min Bridgehampton
     
    Booking.comFrom $2000
    View Deal
  • Victorian Seasons 1 bedroom Carriage House Duplex
    Victorian Seasons 1 bedroom Carriage House Duplex
    Excellent
    HolidayLettingsFrom $487
    View Deal
  • holiday home for max. 8 persons in Bridgehampton, NewYork
    holiday home for max. 8 persons in Bridgehampton, NewYork
     
    TUIVillasFrom $3574
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See all 254 vacation rentals in Southold

Southold Vacation Rentals with a Pool

  • Waterfront carriage house studio
    Waterfront carriage house studio
    Excellent
    AirbnbFrom $382
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  • Southold waterfront 4 bedroom home and cabana
    Southold waterfront 4 bedroom home and cabana
     
    AirbnbFrom $972
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  • Water's Edge First Floor Condo!
    Water's Edge First Floor Condo!
     
    AirbnbFrom $752
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  • Sunny Country cottage
    Sunny Country cottage
    Excellent
    AirbnbFrom $230
    View Deal
See all vacation rentals in Southold with a pool

Southold Vacation Rentals with Wi-Fi

  • Beachwood Manor
    Beachwood Manor
    Excellent
    AirbnbFrom $702
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  • Ground floor 1 bedroom apartment close to it all!!
    Ground floor 1 bedroom apartment close to it all!!
    Excellent
    AirbnbFrom $347
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  • Shelter Island- Classic Water-view Beach House
    Shelter Island- Classic Water-view Beach House
    Excellent
    AirbnbFrom $554
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  • ★ Shelter Island Retreat ★
    ★ Shelter Island Retreat ★
    Excellent
    AirbnbFrom $1079
    View Deal
See all vacation rentals in Southold with WiFis

Southold Pet-Friendly Vacation Rentals

  • Midcentury Modern House on 1 Acre
    Midcentury Modern House on 1 Acre
    Excellent
    AirbnbFrom $648
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  • BRAND NEW Romantic 2br Cottage On YOUR Beach
    BRAND NEW Romantic 2br Cottage On YOUR Beach
    Excellent
    AirbnbFrom $902
    View Deal
  • Sag Harbor Apartment
    Sag Harbor Apartment
     
    AirbnbFrom $385
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  • Charming Southampton Cottage
    Charming Southampton Cottage
    Excellent
    AirbnbFrom $365
    View Deal
See all vacation rentals 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

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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

81º 34º
2.63
89º 37º
1.93
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
May
Jun
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Aug
Sep
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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

Vacation Rentals in Southold

Browse places to stay from all your favorite providers including Airbnb, VRBO, Homeaway and many more at AllTheRooms.com. AllTheRooms has 254 vacation rentals, hotels and other great places to stay while you enjoy Southold, with everything from budget hostels and homestays to luxury Airbnbs and hotels. For those wanting to keep costs down, the lowest priced place to stay in Southold is only $75 a night. On average, an accommodation in Southold will cost you $757 per night.

Those needing to get some work done during their trip to Southold can pick from 169 places to stay that include WiFi. We have 3 accommodations that come with breakfast included. You can maintain your workout routine by staying at one of 12 accommodations that provide gym facilities. If you are driving to Southold, you'll want to pick from 163 places to stay that provide parking. We track 19 places to stay that have a pool or jacuzzi.

AllTheRooms has 50 pet-friendly places to stay in Southold, so if you're traveling with your cat or dog you won't have any problems.

In Southold AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 4 providers, including 97 places to stay from Airbnb, 36 accommodations from VRBO and 36 places to stay from Homeaway.

131 of our accommodations in Southold have been reviewed by previous guests. They rated 48% as great. 45 accommodations allow instant booking.

Destinations near Southold

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