Top Condo Rentals in Town of Southold Town in 2026

A white colonial-style house with a green roof and a lighthouse tower.

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Top Cities in Town of Southold Town

A coastal landscape with a sandy beach, calm water, and scattered trees.

Our top choices for Town of Southold Town condo rentals

A sunset view from a balcony overlooking a calm sea.

1. Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport

Olga P.

2. Mattituck Marvel

Mattituck

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Top Town of Southold Town Hotel Reviews

Sound View Greenport

10/10 Excellent

"A Beautiful and Peaceful Stay at Sound View Greenport I had a wonderful stay at Sound View Greenport and would highly recommend it to anyone looking for a relaxing getaway on the North Fork of Long Island. It’s a great place for couples, families, or anyone who simply wants to escape the busy city and enjoy some quiet time by the water. Greenport is also nearby, making it convenient to explore the local restaurants, shops, vineyards, and other attractions. If you’re planning a trip to Greenport or the North Fork, Sound View is definitely a place worth considering. I would happily stay here again! 🌅🌊❤️"

North Fork Resort

8/10 Good

"My sisters and I booked a 2 bedroom cottage for a long weekend around Greenport. The listing said it was a 2 bedroom with queen beds but when I arrived I realized one room was only a full so one of us had to sleep on the pull out couch for us all to be comfortable. You also definitely need a car. It’s a 45 min walk from the train station so if you’re coming from the city it’s not a convenient location and it’s off a busy road. The cottage did have lots of kitchen amenities and a grill which is great if you’re looking for some easy meals. The shower’s water pressure was great and the air conditioning was effective. Unfortunately you can’t open any windows because there are no screens in the windows and the area is buggy. Overall, the place was nice but the rooms are smaller than I expected and you’re far from everything (even the main reception and pool)"

Fabulous Waterfront Property in the Heart of Wine Country

10/10 Excellent

"Wonderful peaceful location. Comfortable home for our stay for a big family wedding. Short walk to a great sunset beach. The view from the deck in back is a vacation by itself. We really enjoyed our stay and slept well."

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Town of Southold Town Condo Rentals information

Number of reviews	88
Accommodation	2 Condo Rentals
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Treat yourself

Be picky

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Top Cities in Town of Southold Town

East Marion

Our top choices for Town of Southold Town condo rentals

1. Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

2. Mattituck Marvel

Find holiday rentals that suit your style

Top Town of Southold Town Hotel Reviews

Sound View Greenport

Aqua Vista

Silver Sands Motel & Beach Bungalows

North Fork Resort

Beach, Pool, Wine, Shopping!

Cliffside Resort Condominiums

The SandPiper

The Shoals Suites and Slips

Fabulous Waterfront Property in the Heart of Wine Country

Find out more about Town of Southold Town

Town of Southold Town Condo Rentals information