What are the top rated Cottage Rentals in Town of Southold Town?

There are a lot of options in Town of Southold Town. If you plan on staying in the Town of Southold Town area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Town of Southold Town: <a href="/property/charming-cottage/HA-3213126341" class="class="static-page-link"">Charming Cottage</a> <a href="/property/one-of-a-kind-resort-like-waterfront-cottage-in-wine-country/HA-321587073" class="class="static-page-link"">One Of A Kind, Resort- Like Waterfront Cottage In Wine Country</a> <a href="/property/beachfront-endless-sunsets-sandy-beach-cozy-sunroom-open-concept-kitchen/HA-321896250" class="class="static-page-link"">Beachfront - endless sunsets, sandy beach, cozy sunroom &amp; open concept kitchen</a> <a href="/property/incredible-beachfront-home-w-private-beach/HA-3212667933" class="class="static-page-link"">Incredible Beachfront Home w/Private Beach!</a> <a href="/property/stunning-waterfront-newly-renovated-cottage-with-deck-on-water/HA-3212403304" class="class="static-page-link"">Stunning, Waterfront, newly renovated cottage with deck on water.</a> <a href="/property/spring-discount-cottage-on-long-island-sound-private-beach-glorious-sunsets/HA-121297578" class="class="static-page-link"">SPRING DISCOUNT - COTTAGE ON LONG ISLAND SOUND, PRIVATE BEACH, GLORIOUS SUNSETS</a> <a href="/property/waterfront-guest-cottage/HA-3213785227" class="class="static-page-link"">Waterfront Guest Cottage</a> <a href="/property/beautiful-charming-1930s-fully-renovated-cottage-walking-distance-to-the-beach/HA-3214097126" class="class="static-page-link"">Beautiful charming 1930s fully renovated cottage walking distance to the beach!</a> <a href="/property/peaceful-clean-cottage-10-min-walk-to-town-monthly-rates-fenced-backyard/HA-3212885431" class="class="static-page-link"">Peaceful, clean cottage, 10 min walk to town. Monthly rates. Fenced backyard</a> <a href="/property/the-melody-too/HA-3212145264" class="class="static-page-link"">The Melody Too</a>

How much does it cost to rent a cottage in Town of Southold Town?

The average cost for a cottage rental in Town of Southold Town is $514 per night. Xreservations has a wide list of great cottages near Town of Southold Town that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Town of Southold Town that allow pets?

Yes, here are the top cottage rentals in Town of Southold Town that allow you to bring your pet: 'The Gate House'on Beach front Estate with Dockage. Walk to Village . The Endless Summer Cottage North Fork Cottages & RV Resort Cottage on Beach front Estate with Dockage .Walk to Village <a href="/all/usa/new-york/town-of-southold-town" class="class="static-page-link"">See all pet-friendly vacation rentals in Town of Southold Town on Xreservations</a>

Do you have any rental cottages in Town of Southold Town that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Town of Southold Town to find one that works for you.

Are there quality cottages in Town of Southold Town that have indoor swimming pools?

As of 2026, the data from Xreservations shows that there are Over 82 private swimming pools or cottages with indoor pools in the Town of Southold Town area along with other great amenities.

Town of Southold Town Cottage Rentals By Owner

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

From US $480

9.8 (102 Reviews)

Cottage

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Air Conditioner
Parking
Pet Friendly

Town of Southold Town Cottage Rentals & Holiday Homes

Find the best cottages in Town of Southold Town - We found 82 exact matches

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