I think a wildflower garden will allow the perfect transition to a more cottagey appearance since so many of us grow wildflowers in our gardens. They are often the "filler" between perennial plantings!
How tall is your foundation? Some of us have very low foundation areas due to porches, or no basements...some of us have taller (or mixed height) foundations. Old fashioned flowering shrubs often fill the bill in a cottage garden. So many of them now have more modern cultivars including dwarf and low growing option for low foundations. Broadleaf or evergreens fill in between the old fashioned deciduous flowering shrubs and in areas where you want garden next to the house without a shrub, a well placed trellis with clematis, roses (and/or, that is) is a beautiful addition to fill up a blank wall, or even to surround a window area.

Examples at my pink house are: larger gardenia (broadleaf evergreen here), under planted with some sedum that are evergreen and purple leaf clover. In the middle of that small bed is another low growing gardenina. Beside, on the very corner is a beautiful purple leaf deciduous 9 Bark that is pruned into an upright fountain form (it's the form that makes it look good in winter) and underplanted with very low growing, small leaf japanese boxwood (evergreen). Mix of old and new, and balancing leaf color looks great. The plants here had to be very shade tolerant but take a great deal of heat.
The other side has a window and a taller foundation area, and is larger. So on either end there is a purple lorapetalum which are evergreen here. The middle has a pink knockout rose and in front of that is a purple leaf barberry. In front of the lorapetalum are ground hugging variegated abelias. Behind each of the lorapetalum, surrounding the center window is a climbing rose that blooms only in spring and is gorgeous and highly scented. I've used wires and s-hooks to make a trellis because the house is wood sided.
You may not be able to grow those particular plants in your garden (climate) but you could grow something similar. I take care to make sure anything under windows will grow to the height below the windows and doesn't need constant pruning (many shrubs don't look good pruned too much, and of course, some look best when pruned to a formal shape). Mix leaf shape, leaf color and bloom times and it will be pretty and interesting.
I'm currently working on a large expansive side of the house that has a very high foundation and windows 2nd story height. I planted a garden bed in front, and will be adding a group of trellises to the wall that someone just gave me, then adding roses to the trellis. I am going to use a rose I already have that blooms non-stop all summer and in intense heat (that side of the house is very hot).

Roses! Roses are perfect for foundation planting, as long as they aren't planted directly under the drip line. My favorite are old fashioned roses, like damasks, albas, gallicas, etc. Since we have deer, I have to put my roses as close to the house as possible...and then plant bee balm, daisies, coneflowers, cosmos, peonies, lavender, salvias and other deer resistant plants in front of them. Hidcote lavender works really well, as a border in the front, since the deer don't like the smell, they stay fairly tidy and they're hardy to zone 4 :)

GGG- Thanks for the thorough suggestions. Several things I had not thought of, especially the height of foundation plantings. With the wildflower approach, I just threw everything everywhere, without regard to height. Sometimes it worked, sometimes not. I also forgot about flowering shrubs- thanks!
I will check out some of those groundcovers and plants you mentioned. Perhaps I can find some seeds and wintersow them.

LavenderLass- Thanks for the deer resistant suggestion- I will definitely need that. Lots of deer here.

Can't wait to get started, thanks again ladies.

Pufftrinket- Although we have similar zones, I'm sure our climates are much different. Being in eastern Washington, we have dry, hot summers and cold, snowy winters. I'm guessing you have a lot more humidity, than we do. The key to roses is finding ones that are happy, in your area. If you do, they won't take much work at all! I just plant and water...seriously.

When you plant them, we have clay soil, and I find that a lot of aged horse manure does wonders. Once they get a good start, they just take lots of water...that's why the Hidcote lavender is nice, since it doesn't mind a lot of water, either. Most lavenders hate water, but Hidcote is an English lavender...it rains a lot in England, right?

I never spray my roses with anything and they do beautifully. I think part of the reason they do so well, is that I leave a few weeds in the garden, especially in the back. They look a lot like baby's breath and other cottage/meadow plants, so no one seems to notice...but the ladybugs love them. When the aphids show up (and they always do) the ladybugs eat them all and I don't have to spray a thing.

Roses are so much easier than most people think. I don't even winterize mine...you shouldn't have to, if you pick a rose that's hardy in your area. Just don't prune them in the fall, since cold weather can go right into their roots. I hardly ever prune mine, anyway, but if they need to have a few dead or crossed branches removed...do it in the spring, when the forsythias bloom. That really works!

Best of luck with your gardens and try a few roses, if you can hide them up against the house and away from the deer. I think you'll really like them and be very surprised at how easy they can be. Fussy roses are usually just roses that aren't meant to be grown in your area. If you need more suggestions for your area, try the Roses and/or Antique Roses forums :)

LL, my dad grew roses back home in Indiana. I knew hybrids were a challenge in the south. I was never willing to do the necessary spraying for black spot & mildew. When I learned about antique roses I thought they might be the answer, but the love just isn't there.

I planted 2 Little Pinkies fall of 2010. One caned beautifully (is that the correct term?), the other sat there never getting taller than a couple feet. This fall I pulled the short one and replaced it with jasmine and honeysuckle. The other one has climbed up and over the arbor and actually has a couple blooms right now, but I'm fighting the urge to cut it back and pull it out too.

Natal- I know that tea roses and noisettes are popular in Florida...would they grow well, in your climate? Sometimes ramblers are nice, too. I wish I could grow more (it's too cold) but I do have a couple of Veilchenblaus and a Bleu Magenta, by the porch...or what was my porch.

I'd love to grow a Paul's Himalayan Musk rose, but it's zone 6, minimum. Much like Celsiana, they seem to start out light pink and turn white, as they age. Here's a picture...they're just beautiful and they're supposed to have a wonderful fragrance :) {{gwi:767476}}From Lavender's Garden

LL, I have no idea. I think I'm just not a rose person. I do enjoy receiving some every now and then. We have a guy in the neighborhood with a passion for roses. He has hundreds of bushes and maintains many more for other people. He usually shares a bouquet a couple times a year with many of the neighbors. This is one from last year.