Photo by Benny Goh

Southold apartments

We found 31 apartments — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in an apartment holiday rental in Southold?
A number of factors will determine the price of an apartment holiday rental in Southold, such as the size of the property and when and how long you're travelling. All you need to do is enter your travel dates and preferences to find a condo that fits your style and budget.
When is the best time to rent a holiday condo in Southold?
Read reviews and seek recommendations from others who have visited Southold during different times of the year. Their experiences can provide valuable insights and help you decide when to lock in your apartment holiday rental. Also be aware of local holidays or major events, as these periods may see increased tourist activity and affect pricing.
Where can I rent a Southold holiday apartment with great views?
Open the curtains or blinds of your apartment holiday rental in Southold and you can admire amazing views of historic areas. Want an extra special touch? Browse for condos with a balcony and take in the scenery while drinking your morning brew.
Does Southold have any weekend apartment rentals?
Switch on your out-of-office reply and venture to Southold for a weekend break in a Stayz apartment holiday rental. A top tip? Stay flexible with your preferred dates and book ahead to have the first choice of some fabulous holiday condo rentals.
Can I book a luxury apartment in Southold?
For a taste of the high life, choose one of our luxury apartment holiday rentals in Southold. Alongside practical amenities like living spaces and multiple bedrooms, you'll also have access to perks like hot tubs and pools. All you have to do is search for holiday condo rentals on Stayz that are rated highly by guests and narrow your results based on your ideal amenities and features.
What are the top things to do in Southold?
Get your Southold escape off to an amazing start by visiting popular sights like The Hamptons Beaches, Orient Point County Park and 67 Steps Beach. Stay in a Stayz apartment holiday rental with the family and then explore the best of this destination together.
Why should I book my apartment holiday rental with Stayz?
You can book your apartment holiday rental with confidence and peace of mind on Stayz. From the minute you book and pay for your reservation until your getaway is over, we'll be there for you every step of the way. It's part of our Book with Confidence Guarantee. If you have to cancel, we've got your back too. Most of our properties come with flexible cancellation policies