Nestled along Squaw Peak Road, Lily Pad's Landing offers an intimate bed & breakfast experience where timeless elegance meets the quiet beauty of western Massachusetts.
Lily Pad's Landing is more than a place to stay — it is an invitation to slow down, to savor the unhurried rhythm of life in the Berkshires. Our historic estate, set among mature maple and oak trees just outside Great Barrington's village center, offers five individually furnished guest rooms, each named for a local landmark and thoughtfully appointed with antiques, linens, and the subtle comforts of a home rather than a hotel.
Whether you are here for a weekend of gallery-hopping, a romantic escape, or simply the desire to wake to birdsong and the smell of fresh-baked sourdough, we welcome you to make this your temporary address.
Our ExperienceEach guest room is a distinct space — furnished with care, layered with texture, and designed to feel like a room you have always wanted to sleep in.
Most Popular
Our largest room, featuring a king bed, private sitting area, and panoramic views of the surrounding ridgeline. The en-suite bath includes a deep soaker tub.
Named for the river that runs through our valley, this queen room features soft blues and warm woods, with a desk perfect for writing.
Dressed in forest greens and taupes, this cozy queen room overlooks the property's garden path and is steps from the morning porch.
Our most intimate room, with a full bed and warm terracotta accents — a quiet retreat for the solo traveler or couple seeking simplicity.
Bright and sunlit with two twin beds, this room is ideal for friends or siblings. Its light palette and open windows make it feel like a morning dream.
With only five guest rooms, every visit is treated with the same care and attention as a dinner hosted for close friends. We know our guests by name.
Check-in is flexible. Breakfast is served when you are ready. There is no schedule to keep here — only the gentle rhythm of the Berkshire seasons.
We guide our guests to the best trails, the quietest bookshops, and the restaurants that locals actually love — not the ones in the guidebooks.
Whether you are celebrating an anniversary or simply need a weekend to yourself, Lily Pad's Landing is designed to restore your sense of calm.
Our two acres of mature landscaping include a winding stone path, a koi-lined pond, rose gardens that bloom through September, and a shaded porch where morning coffee is best enjoyed in silence. The property borders open woodland — deer are regular morning visitors, and in late summer, the fireflies turn the dusk golden.
Great Barrington's village center, with its restaurants, galleries, and the historic Barrington Theatre, is a short drive away. We are also within easy reach of Stockbridge, Lenox, and the Tanglewood grounds.
Each morning, our breakfast is prepared from local ingredients — eggs from nearby farms, bread baked the night before, seasonal fruit from the orchards of south-central Massachusetts. Menus change with the seasons, and every meal is an opportunity to taste the region.
We accommodate dietary needs with advance notice. Coffee is freshly ground. Tea is selected each week. There are no rush-hour clocks here.
We welcome guests year-round and recommend booking in advance, particularly for the fall foliage season and winter holiday weekends. To check availability or plan your visit, please call us directly.
