Boarding multiple dogs. When you have multiple dogs to board, there are a few extra considerations to bear in mind. Some kennels offer discounts for boarding multiple pets, and this is a good option to consider if offered. Depending on your dogs’ sizes and temperament, boarding two dogs to a kennel may work. Smaller dogs with insecurity issues who share food and sleeping areas willingly may benefit from shared spaces. However, you want to avoid this option if any of your dogs have food possession issues. Another thing to keep in mind is that the kennel environment is a new, different experience regardless of whether your dogs are kenneled together.