Southold cottages

We found 64 cottages — enter your dates for availability

Find spaces that suit your style

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  • 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

Are there any cottage rentals in Southold?
Choose one of our 64 cottage rentals in Southold and enjoy the charm, comfort and unique experiences that come with this type of property. Greenport West, Silver Beach and The Heights are among the city's most popular neighbourhoods.
How much does it cost to stay in a cottage rental in Southold?
One of the only things better than spending your break in a comfy cottage rental in Southold is getting it for a fantastic price. Keep an eye out for any properties offering discounts to guests who book a week. Some properties offer even better discounts if you stay an entire month. You can also use Bookabach's price filter to look for cottages that match your budget.
When is the best time to rent a cottage in Southold?
First, consider if you prefer the energy of peak season or the quieter vibe of low season. Also think about factors like seasonal temperatures and what you want to do in Southold. Whenever you visit, there'll be a cottage rental ready to welcome you.
Where can I rent a Southold holiday cottage with great views?
Book a cottage rental in Southold and you'll be stepping out of your front door to fabulous vistas. Some of our more popular cottages here come with views of historic areas.
Does Southold have any lakeside cottages?
Stunning views of glittering water, the tranquility of nature and outdoor recreation are just some of the things you can look forward to in one of Bookabach's lakeside cottage rentals. Use our handy "Location" filter and check the "Lake" box to see if there are any cosy stays in Southold overlooking the water.
What are the top things to do in Southold?
When it's time to go beyond the idyllic surroundings of your cottage rental, you'll discover plenty to do and see in Southold, starting with The Hamptons Beaches. Looking for more things that will keep the whole family occupied? Orient Point County Park and 67 Steps Beach are other leading attractions worth visiting.
Why should I book my holiday cottage with Bookabach?
Booking a cottage rental with Bookabach means you'll have the whole place to yourselves — your own private oasis, with no interruptions or distractions from anyone else. What's more, our easy payment and cancellation policies allow you to modify your plans if you need to.