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Southold Long Term Vacation Rentals(23)

23 Results
$300 - $450
per night
2 - 3 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 5
2 - 3 night minimum stay
$200
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 night minimum stay
2 Reviews
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 - 7 night minimum stay
$225 - $300
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(9)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
1 Review
$490 - $821
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
$190 - $275
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(9)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(3)
  • 4 BR,
  • 3 BA,
  • Sleeps 13
2 - 7 night minimum stay
(5)
$300 - $350
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 night minimum stay
$175 - $195
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(10)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(3)
$180 - $195
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(7)
$650
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 3 night minimum stay
$642 - $3,500
per week
7 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 - 30 night minimum stay
8 more choices from the HomeAway Network
$3,000 - $8,167
per week
2 - 31 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 - 31 night minimum stay
$536 - $650
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
$300
per night
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
3 night minimum stay
1 Review
$600 - $700
per night
2 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
1 Review
$429 - $1,000
per night
4 - 11 night minimum stay
  • 4 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 14
4 - 11 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 night minimum stay
1 Review
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Recent Southold Reviews

Wonderful cottage - perfect location!

5 of 5
My husband and I enjoyed our week long stay at the cottage. Comfortable and cozy with easy access to wineries, restaurants and the beach! Added bonus of the hot tub and lake make it a perfect get away.
  • Submitted: Sep 4, 2014
  • Stayed: Jul 2014

cute rustic cottage with great location

5 of 5
My husband and I stayed here for Labor Day weekend, and were thrilled with the cottage. It was the perfect space for 2 people (although you could squeeze an extra 2 in on the sofabed if you're really desperate). We loved the old hardwood floors and quaint details, and the location was great: 10 min. walk to Kenney's Beach, and within a 10 min. drive to many of the local farms and wineries. The kitchen was fully stocked, including a big pot and kitchen shears for cooking lobsters, and a grill with direct gas line. We enjoyed cooking our farm fresh ingredients there most nights. There were plenty of towels, but bring your own hair dryer. We were so sad to leave, and would definitely consider renting here again.
  • Submitted: Sep 2, 2014
  • Stayed: Aug 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