Massachusetts is about 223 times bigger than Anguilla.

Anguilla is approximately 91 sq km, while Massachusetts is approximately 20,306 sq km, making Massachusetts 22,214% larger than Anguilla. Meanwhile, the population of Anguilla is ~18,741 people (6.5 million more people live in Massachusetts).
Tip: This to-scale comparison of Anguilla vs. Massachusetts uses the Mercator projection, which distorts the size of regions near the poles.