Ulwell Cottage was the very first site I ever camped at, about 4 years ago. I hadn't booked and just turned up there and they gave me a pitch just behind the reception which was under some trees in front of the play area. I have a feeling it might have been pitch 12?
It was fairly flat there and of course a short distance to the entrance and the pub. The pub, incidentally, is also the local pub and not just for campers. I found the food excellent although a little expensive but better than going into Swanage and paying the extortionate parking fees...you need a credit card to park there!!
The downside was that the whole camp is quite hilly and the nearest toilet was a good couple of minutes uphill walk away. Not too bad for me but not good for anyone with walking difficulties. It's a nice, well kept site but I wouldn't recommend it to anyone with walking difficulties. The pitches themselves are fairly flat as I recall but the site itself isn't the easiest to negotiate.
There is another campsite in the town itself called Cauldron Barn Farm, only 10 minutes slow walk to the seafront, but again, although the pitches themselves are flat the area is generally hilly (see the UKCS reviews)...not exceptionally so but quite tiring on the old legs.
Perhaps the flattest site I have been to along that stretch of coast is West Fleet Farm near Weymouth (no caravans). The entire campsite is pretty well a big flat field seperated into sections by low walls, trees and shrubs and very well maintained. It has it's own bar/restaurant with entertainment in the evenings but isn't a large commercial site. The downside is that it's in the middle of nowhere about 4 miles from Weymouth...parking at Weymouth is a heck of a lot more reasonably priced and more plentiful than Swanage though.
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