Stay: Shandaken Inn
Outfitted in clapboard of its signature "Shandaken blue," this adorable bed and breakfast has been around almost 100 years, serving as a social hot spot in the Catskills since the 1920s. There are only 15 guest rooms (each uniquely furnished and named for one of the local summer camps and resorts that once reigned in the region), along with an in-house bar and restaurant (serving farm-to-table fare), and living room-like common areas that encourage guests to hang out like they're all at some tasteful relative's country home.
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[Photo via Shandaken Inn]
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