When the former head of J.Crew's menswear and an artist open a bed and breakfast, you get The Inn at Kenmore Hall. The five-bedroom hotel is housed in a 1792 Georgian estate, nestled on 20 wooded acres in the Berkshires. Each room is impeccably designed, fusing the home's historic architecture with a unique mix of antiques and mid-century modern pieces. From the wood-burning fireplaces to the personal collection of books and artwork, the cozy atmosphere feels more like you're a guest at the couple's home rather than paying patrons. For a more secluded stay, opt for the Carriage House Cottage. Located across the courtyard from the main house, the space offers its own living area, kitchenette, and a private porch to admire the surrounding orchards.