There are some really cool places to visit where you can enjoy a vacation rental with access to kayaking.
Twin Lakes Resort is a paddler’s dream as no motorized boats are allowed. It is in a rather remote area between the Willamette Valley and Bend. The drive is beautiful along the Cascade Lakes Scenic Byway. Not really known for wine and more renowned for its craft beer, Bend is relatively close and a fun town for all ages. If you are more adventurous you can explore the Deschutes Paddle Trail.
Crescent Lake Resort is a beautiful lake near many other lakes that can be explored by kayak. Cabins line the lake. Explore nearby Waldo Lake- one of Oregon’s purest lakes where motorized boats are banned.
Cove Palisades State Park has some really cool cabins along the water. Like Twin Lakes Resort it is in a rather remote area.
Loon Lake Lodge is located along the beautiful Oregon Coast near Reedsport on Loon Lake where you can enjoy kayaking. You can pass through two different wine regions to get here- Southern Oregon (known for Cabernet and Syrah) and the South Willamette Valley (known for its Pinot varieties).
There are more, but these seem to me to be the most family friendly, with great kayaking opportunities. I hope this helps. Let me know if you have any more questions.