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Southold Vacation Rentals(78)

78 Results
$429 - $1,100
per night
2 - 14 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 - 14 night minimum stay
(10)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(17)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 14 night minimum stay
(10)
$300 - $386
per night
2 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 5
2 - 7 night minimum stay
$200
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 night minimum stay
2 Reviews
  • 5 BR,
  • 2 BA,
  • Sleeps 6
$12,500
per month
30 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
30 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
  • 5 BR,
  • 1 BA,
  • Sleeps 10
5 night minimum stay
$250 - $300
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
2 - 7 night minimum stay
(31)
$300 - $529
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
1 Review
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(7)
$300
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(9)
$2,350 - $3,850
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(13)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
1 Review
$200 - $375
per night
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night minimum stay
(42)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(3)
$300 - $350
per night
2 - 5 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 5 night minimum stay
(15)
$3,150
per week
7 - 14 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 6
7 - 14 night minimum stay
2 Reviews
$190 - $275
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(9)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(3)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
$386 - $550
per night
2 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(5)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
(6)
$300 - $1,250
per night
2 - 3 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
(73)
$250
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(5)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
(4)
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Recent Southold Reviews

Excellent Cottage!

5 of 5
We had such a nice time at this north shore cottage. Its quiet and scenic....a perfect spot!
  • Submitted: Dec 12, 2014
  • Stayed: Nov 2014

Autumn at the Wineries

5 of 5
My family and I stayed here for a long weekend this fall. The house is beautiful - very clean and comfortable. Perfect for families with children. 15 min drive to downtown Greenport. The owners were VERY friendly and quick to address and resolve any issues. Location is right on the creek - perfect for boating and kayaking. House is all one level except for one step in to the home - good for elderly/disabled. I would love to rent this property again - it is pure relaxation. Thank you to Tim and Nancy for such a great stay.
  • Submitted: Nov 6, 2014
  • Stayed: Oct 2014

Romantic Getaway

5 of 5
4 kids, 2 cats, and a dog don't leave much time for parents to connect. This cottage rental just steps from the beach, a quick walk to town and in the heart of wine country was just what the doctor ordered! The house was very cute, well kept, and contained everything we needed for sunny breakfasts while reading the Times (remember those days?) and cozy dinners laughing over a bottle of wine picked up at our favorite Vineyard, Old Field. Great location, great house.
  • Submitted: Oct 14, 2014
  • Stayed: Oct 2014