Find Vacation Rentals in Southold

We have 15 properties to choose from
Southold
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Southold
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Popular Southold Vacation Rentals

Find the perfect Southold vacation rental

House Southold
$290 per night
House ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding (13 ratings)
Southold, Suffolk County, New York, United States
Details
Vacasa
Details
Details
Bed and breakfast Southold
$617 per night
Bed and breakfast ∙ 8 guests ∙ 1 bedroom
4.9
Outstanding (26 ratings)
Southold, Suffolk County, New York, United States
Details
Expedia
Details
Details
House Southold
$406 per night
House ∙ 8 guests ∙ 3 bedrooms
4.7
Excellent (20 ratings)
Southold, Suffolk County, New York, United States
Details
Vrbo
Details
Details
Bed and breakfast Southold
$720 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (18 ratings)
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Details
Bed and breakfast Southold
$617 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (18 ratings)
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Details
Bed and breakfast Southold
$771 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (18 ratings)
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Details
Bed and breakfast Southold
$617 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (18 ratings)
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Details
Bed and breakfast Southold
$617 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (18 ratings)
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Details
Bed and breakfast Southold
$898 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (18 ratings)
Southold, Suffolk County, New York, United States
Details
HomeToGo
Details
Details
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Recommended Rentals With Pools

House  Southold
$495 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding (48 ratings)
Southold, Suffolk County, New York, United States
Pool
Details
Vrbo
Details
Details
House  Southold
$289 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (4 ratings)
Southold, Suffolk County, New York, United States
Pool
Details
Vrbo
Details
Details
House  Southold
$799 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (31 ratings)
Southold, Suffolk County, New York, United States
Pool
Details
Vrbo
Details
Details
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Pet-Friendly Homes and Apartments

House  Southold
$323 per night
House ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding (13 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
Cottage  Southold
$104 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (100 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
Cottage  Southold
$129 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (79 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
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Best vacation rentals with a balcony

House  Southold
$257 per night
House ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (5 ratings)
Southold, Suffolk County, New York, United States
Balcony
Details
Vrbo
Details
Details
House  Southold
$390 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (28 ratings)
Southold, Suffolk County, New York, United States
Balcony
Details
Vrbo
Details
Details
Cottage  Southold
$222 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (4 ratings)
Southold, Suffolk County, New York, United States
Balcony
Details
Vrbo
Details
Details
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Frequently Asked Questions

How much does a night in a vacation rental cost in Southold on average?

Prices for a stay in Southold begin at $118 per night.

Are there any vacation rentals available to book in Southold?

Tripping.com offers great selection on vacation rentals with 15 offers currently available in Southold.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Southold

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Southold offers 270 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Southold start at an average price of $413 a night with long-term rentals averaging $25 a month. These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 243 of Southold’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 50 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 236 vacation home rentals. Traveling with your dog or cat? Choose from 71 pet-friendly rentals in Southold that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go! Search properties from 6 vacation rental sites in Southold where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 216 HomeAway rentals, 26 TripAdvisor short term rentals and 16 Booking.com vacation rentals.

Popular Day Trips Near Southold

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