This paper presents VMFlockMS, a migration service optimized for cross-datacenter transfer and instantiation of groups of virtual machine (VM) images that comprise an application-level solution (e.g., a three-tier web application). We dub these groups of related VM images VMFlocks. VMFlockMS employs two main techniques: first, data deduplication within the VMFlock to be migrated and between the VMFlock and the data already present at the destination datacenter, and, second, accelerated instantiation of the application at the target datacenter after transferring only a partial set of data blocks and prioritization of the remaining data based on previously observed access patterns originating from the running VMs. VMFlockMS is designed to be deployed as a set of virtual appliances which make efficient use of the available cloud resources to locally access and deduplicate the images and data in a distributed fashion with minimal requirements imposed on the cloud API to access the VM image repository. VMFlockMS provides an incrementally scalable and high-performance migration service. Our evaluation shows that VMFlockMS can reduce the data volumes to be transferred over the network to as low as 3% of the original VMFlock size, enables the complete transfer of the VM images belonging to a VMFlock over transcontinental link up to 3.5x faster than alternative approaches, and enables booting these VM images with as little as 5% of the compressed VMFlock data available at the destination. © 2011 ACM.