33 Main

33 Main is a true delight in the heart of Lenox. From the moment you step inside, you’re wrapped in warmth, style, and thoughtful hospitality. The inn is beautifully appointed—elegant yet cozy—with every detail carefully curated, from plush linens to perfectly arranged sitting areas that invite you to linger. One of the unexpected highlights? The cookies. Baked fresh daily, they’re the kind of comfort that makes you feel instantly at home—warm, delicious, and always waiting for you in the kitchen like a little gift after a day exploring the Berkshires. The staff is gracious and genuinely kind, offering just the right balance of attentiveness and privacy. Whether you’re sipping wine on the front porch or wandering to nearby shops and restaurants, 33 Main feels like a home away from home—only more beautiful and far more relaxing. A perfect escape in one of New England’s most charming towns. We can’t wait to return.

Adorable boutique hotel offering a wide variety of extras. The room we stayed in was exquisite. East entry with pad lock and key. Breakfast was included and a nice touch. Perfect location for Tanglewood or center of town. Dog friendly

We had an amazing weekend at the beautiful 33 Main. Check-in was seamless despite our after hours arrival. We stayed in the beautiful and comfy Sunnyholm suite. The soaking tub was relaxing and provided a spa like experience. Breakfast was delicious each morning and the always available chocolate chip cookies were such a nice treat. The location was perfect for exploring downtown Lenox. We look forward to returning to 33 Main.