1. USA
  2. New York
  3. Southold
  4. Cottage Rentals

Southold Cottage Rentals & Holiday Homes

Find the best cottages in Southold - We found 20 exact matches

About Southold Cottage Rentals on Casai.nz

Searching for cottages to rent near Southold? Casai features more than 20 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Southold have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Casai’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Southold.

Are you planning to travel to the lakeside, beach, or mountain area? Casai’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Casai boasts of 20 holiday cottages and places to stay in Southold. The site provides unique Airbnb, VRBO, Casai-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

Show more
Show less

Frequently Asked Questions About Southold Rental Cottages

The average cost for a cottage rental in Southold is $430 per night. Casai has a wide list of great cottages near Southold that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Southold that allow you to bring your pet:

See all pet-friendly vacation rentals in Southold on Casai.nz

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Southold to find one that works for you.
As of 2026, the data from Casai.nz shows that there are Over 20 private swimming pools or cottages with indoor pools in the Southold area along with other great amenities.
About 20 cottages in Southold boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Southold on Casai.nz
Yes, there are luxury cottages in Southold. Find more luxury, lakefront, winter, & last-minute cottage rentals near Southold.