The only onsite dining at the Windsor Inn is the free buffet breakfast served each morning in the bright and airy breakfast room that looks out on the English gardens. It's a standard serve-yourself offering, but a cut above the typical continental breakfast. Highlights include a pancake-making machine, which is always fascinating for kids, biscuits and gravy, sausage, fruit, yogurt, toast, and cereal. It's plenty to give the kids enough energy to start a busy day.
For something more substantial, guests only have to walk across the hotel parking lot to the adjoining Oak Tree Northwest Bar and Grill. They serve a hearty breakfast that includes huge omelets, stacks of pancakes, and very tasty eggs benedict. The Oak Tree is also convenient for lunch and dinner if you don't want to stray far from the hotel.
For a night in your room, or even relaxing by the pool, call the nearby Great American Pizza Company if you want a good pizza delivered. However, our recommendation is that you hop in your car and make the 5-minute drive to Martolli's Handmade Pizza for a carryout order of the absolutely best pizza in Ashland. They have two locations in town, so you'll want to hit the closest one across from Southern Oregon University. Unfortunately, they don't deliver anymore, but it will be worth it to your family to go get it yourself. Their pizzas are all freshly made, and they also have huge salads and calzones. Makes for an awesome pool party back at the hotel.
Some suites at the Windsor Inn contain a kitchenette stocked with pots and pans, so you might want to stock up on groceries at the nearby Albertson's grocery store, a full-service supermarket less than half a mile away. If you're looking to buy local, pay a visit to the downtown Ashland Food Co-Op for a full selection of natural and organic foods, either grown or produced locally. They also have an outstanding deli where you can pick up gluten-free and vegan sandwiches to take back to your room.