The Best Places to Drink and Stay in Woodstock

Each of the four suites at this Woodstock inn is named for a rock and roll matriarch, so you're essentially choosing between Aretha, Carole, Joni, and Stevie. It's a small, sustainably minded boutique hotel with clawfoot tubs, wood-paneled bathrooms, and private patios throughout. Bikes and a hot tub are shared by all guests. Two suites welcome dogs, which feels on-brand for a place that already has strong opinions about who deserves to be on the walls.

1. Michelin Guide Selected Hotels

A boutique bed and breakfast on Woodstock's main drag, Twin Gables keeps a well-preserved Victorian exterior but drops any interest in period charm the moment you walk through the door. Inside, bold colors and graphic art fill rooms that share no common aesthetic with each other. Not every room has a private bathroom, and the ones that do book fast on weekends, so plan accordingly.

1. Michelin Guide Selected Hotels

Bluetooth turntables stocked with actual records sit in every room at this boutique hotel, which feels like a fair summary of Woodstock's relationship with the past. The compound reads as its own little world despite being in the middle of town: modern lines, rustic textures, heated bathroom floors, colorful art. The Tannery café handles coffee and not much more, but the town is right there and seems happy to help.

1. Michelin Guide Selected Hotels