Southold Cottages

A calm lake with a forest in the background during sunset.

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Our top choices for Southold cottages

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

1. North Fork Resort

Greenport

Altynai

includes taxes & fees

1 Nov - 2 Nov

A residential area with houses, a driveway, and a body of water in the background.

2. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...

Lydia

includes taxes & fees

1 Nov - 2 Nov

A deck with a gray sofa, a wooden chair, and a metal fire pit.

3. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport

Jeannette M.

includes taxes & fees

11 Nov - 12 Nov

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

4. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

JM B.

includes taxes & fees

2 Nov - 3 Nov

A single-story house with a gabled roof, a front porch, and a well-maintained garden.

5. Walk to Beach | Seabreeze Cottage #4

Hampton Bays

Weston B.

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a porch, a mailbox, and a lawn.

6. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Madison

Samantha D.

includes taxes & fees

4 Nov - 5 Nov

A white cottage with a front door, a garage, and a small porch with a potted plant.

7. The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton

Wink V.

includes taxes & fees

31 Oct - 1 Nov

A two-story house with a porch, multiple windows, and a front door.

8. Adorable Cottage with Cottage porch, walk to water & town

Westbrook Center

Francine F.

includes taxes & fees

31 Oct - 1 Nov

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Top Southold Hotel Reviews

Faraway Sag Harbor

10/10 Excellent

"Perfect experience all around. But very noisy at 8 am - maintenance trucks, etc too loud. Would be better if they started at 9 am. A little jarring to hear the noise right outside rooms so early"

Zey Hotel

10/10 Excellent

"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of the hydrants was causing the dirty water. The manager promptly told us we could stay until 6:00 pm for free, so that we would be able to take clean showers. We told him that we had showered early, and that we had no problem. But his response showed how he cared for the guests."

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