The handholding was to help direct her back to the hotel in the low light as the sun disappeared beneath the trees and, maybe- he would have to admit to himself- an attempt to keep the connection between them going. The dogs had accepted Franny into their dog gang. Should she need help they would tear someone apart. They were Will's dogs after all.
Back at Will's room, he placed the pillows in the bathroom, gesturing for the dog to make themselves comfortable. Three and a half dogs (Buster being the half) could easily fit in the bathroom comfortably, but they were have been out of luck had his other four dogs been there. Winston gave him a look of knowing and insult that they were being kicked from the room for this, but settled down beside Franny as Buster jumped into the toilet to be above the others.
Pressing his lips together, he turned back to Yelena in the room. "I didn't think I'd ever wish for a suite room at this hotel," he scoffed.