Southold vacation rentals

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Popular amenities for Southold vacation rentals

Stay near Southold's top sights

North Fork Table & Inn86 locals recommend
Croteaux Vineyards70 locals recommend
Sparkling Pointe Vineyards & Winery64 locals recommend
Bedell Cellars62 locals recommend
Southold Fish Market54 locals recommend
Greenport Harbor Brewery and Restaurant54 locals recommend

Quick stats about vacation rentals in Southold

  • Total rentals

    210 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    3.2K reviews

  • Family-friendly rentals

    180 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    60 properties have a pool

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Southold?

    Yes! Work meets play with ease at over 120 vacation rentals in Southold featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Southold?

    Four-legged friends are welcome in Southold. Choose from more than 70 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cottage rentals in Southold?

    Experience the best of Southold with our cottage rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Southold vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Southold, available on Airbnb. Make a splash and soak up the sun in style!

  • Do cottage rentals in Southold have a bbq area?

    Absolutely! We offer over 10 cottage rentals with a bbq area in Southold. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Southold have self check-in?

    Absolutely! We offer over 40 house rentals with self check-in in Southold. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Southold have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Southold. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Southold have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Southold. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Southold?

    Southold has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Cottage Rentals in Southold?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Southold