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Southold Vacation Rentals(74)

74 Results
2 - 14 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
(10)
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
(17)
2 - 14 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
(9)
2 - 3 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 5
$429 - $1,000
per night
4 - 11 night minimum stay
  • 4 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 14
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
1 Review
$490 - $821
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
31 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
(29)
4 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(6)
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
(13)
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
1 Review
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(9)
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(3)
$386 - $600
per night
2 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
(5)
2 - 6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(12)
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(3)
3 - 5 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
(14)
$175 - $200
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
(4)
$2,450 - $3,500
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
(3)
$457 - $800
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
(6)
2 - 3 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
(73)
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Recent Southold Reviews

Lovely House

5 of 5
5 of us make friends stayed here and used it as a base for golf. Beautiful house and location and Chuck was extremely helpful and welcoming. We hope to go back.
  • Submitted: Aug 21, 2014
  • Stayed: Jul 2014

Peaceful oasis

5 of 5
Joan's cottage was a perfect way to kick off the summer. On arrival I immediately felt at home. The place is cozy and perfectly located. It is great for just kicking back and reading in the hammock or walking a block to the beach. Greenport is a short drive and has many great restaurants and shops. Joan was very accommodating and we hope to return next summer. I highly recommend this summer retreat!
  • Submitted: Aug 20, 2014
  • Stayed: Jul 2014

BEST DECISION EVER!

5 of 5
My husband and I rented this cottage for most of the summer and couldn't be happier with it. We lovingly refer to this place as The Pond Shack. The house is small and rustic so if you want a luxurious rental, this isn't for you. But if you want a low key retreat at an unbeatable price in an absolutely gorgeous location with beautiful views of the Great Pond (it's really more of a lake) and a 5 minute walk to the beach, then look no further. This place is perfect for 2 couples or a couple with kids. The pond is clean and not scummy - great for swimming or just watching the water. The best thing about this place is that you feel totally in nature. We've seen a ton of Osprey, swallows, a cardinal and of course geese and there's even a swan that lives on the pond too. There are also turtles in the pond, and deer and rabbits all around the neighborhood. There are great walking/running trails just up the street and of course gorgeous Kenney's Beach with uninterrupted sound-front stretches of sand (and rocks too - bring aqua socks if you have them!). We like to walk over and watch the sunset and the water is calm and great for swimming. The owner Larry is great and we've enjoyed meeting him and interacting with him throughout our stay. He's always been very friendly, responsive and helpful. We love the North Fork and couldn't be happier to have found this gem. So sad the summer's almost over but we will definitely be back!
  • Submitted: Aug 17, 2014
  • Stayed: May 2014