Stay: Callicoon Hills
A favorite of city cool kids coming up for the weekend, Callicoon Hills is a century-old resort marrying modern design with rustic charm. The all-in-one retreat is ideal for all seasons - splash in the pool in the summer, warm up by a fire pit come winter. And even if you check in elsewhere, the hotel's Conover Club restaurant, an ode to old world Americana replete with stone fireplace, is a lively must-visit for dinner and drinks.
[Photo via Callicoon Hills]