Southold Guest Houses

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

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Our top choices for Southold guest houses

A serene landscape with a calm body of water reflecting trees with autumn foliage.

1. House on Chase Creek

The Heights

Calvin

CA $340 total

includes taxes & fees

Oct 5 - Oct 6

A garden with a wooden bench, a playground, and a house in the background.

2. Hampton's Vacation Inn

Hampton Bays

Brian

CA $196 total

includes taxes & fees

Sep 8 - Sep 9

3. New and Modern Bridgehampton Accommodations

Bridgehampton

Peter R.

CA $766 total

includes taxes & fees

Sep 9 - Sep 10

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Top Southold 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)"

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