Yes, we have three fairly small dogs, under 20 pounds, and they all sleep with us. My scruffy little Romeo sleeps with my son, while the rat terrier and the Chihuahua/terrier mix, Lily and Picasso sleep with me.
Now what was rough was when my daughter stayed with me and she was out of town, because her two dogs, a large Chihuahua and a miniature pinscher also slept with me. I only have a full size bed, so with four or sometimes five little dogs, that was a bit much -- especially when they'd growl at each other.
They all sleep under the covers except for Romeo. He has more fur than the other dogs, so that might be a factor.