Historic Inns of the Berkshires

Williamstown · Inn

A full-service inn in the heart of Williamstown, steps from the Clark Art Institute and the Williams College Museum of Art. Sixty-four rooms, a restaurant and bar, fitness center, and the kind of New England innkeeping that has served this particular college town for generations. The town itself — small, walkable, culturally loaded — does a lot of the work.

Lenox · Inn

An 1912 mansion built as a summer estate for the heir of Procter & Gamble, now an eleven-room inn a mile and a half from Tanglewood. Rooms include sleigh beds and working fireplaces. Multiple Yankee 'Best of New England' awards. The Restaurant at the Gateways is a genuine destination — the kind of table that earns its own visit during Tanglewood season.

Lenox · Inn / B&B

Fourteen rooms in a Victorian inn on Walker Street in central Lenox with a seasonal pool and tennis court. Family-owned and operated at a scale where the service stays personal in a way larger properties cannot match. A short walk to Tanglewood and the Church Street restaurant scene.

Lenox · Inn / B&B

A ten-room Victorian inn on a quiet Lenox street, known for an extensive poetry collection, weekend readings, and the kind of literary atmosphere that the town's history — Edith Wharton, Herman Melville, Nathaniel Hawthorne all spent time here — suggests you should be able to find. Massage services on site. A pool. Ten minutes from Tanglewood. One of the better values in a town that has gotten expensive.

Lenox · Inn

A Gilded Age manor on Plunkett Street in Lenox, adjacent to Edith Wharton's estate, The Mount. Rooms in both the historic manor and a more contemporary motel wing. Breakfast buffet included, pool on-site. More affordable than its immediate neighbors on the same road.

Lee · Inn / B&B

A luxury bed and breakfast on 32 acres in Lee — one of those properties that consistently outperforms its surroundings on guest satisfaction. Rooms in a Federal-style main house with fireplaces and whirlpool tubs in the upgraded rooms, heated outdoor pool, tennis court. The balance between historic character and genuine comfort is calibrated well. Convenient to both Lenox and Stockbridge without being in either.

Lee · Inn / B&B

An 1885 schoolhouse on Main Street in Lee converted into nine rooms — the original blackboards and schoolhouse bones are intact. Rooms are oversized by B&B standards; the conversion preserved the high ceilings and natural light that the building was designed around. A genuine historic conversion without the renovation trauma that phrase sometimes implies.

Lee · Inn

Fifty-two rooms on the shores of Laurel Lake in Lee, with kayaking, a pontoon boat, and an Indian restaurant — Mint — with a lake view. A 2016 Yankee Editors' Pick for Best Inn for Paddlers. The lake setting is the draw: less about design, more about the water. A reliable mid-range option in a corridor that can get expensive, with genuine outdoor recreation on-site.

Stockbridge · Inn

One of the oldest continuously operating inns in the country — on Main Street in Stockbridge since the 18th century, and looking like the Norman Rockwell painting it effectively is. One hundred twenty-five rooms, three restaurants, a year-round heated outdoor pool, a gift shop, live entertainment in The Lion's Den. The antique-filled rooms and birdcage elevator are genuine. The town of Stockbridge — compact, historic, walkable — does the rest.

Stockbridge · Inn / B&B

A twelve-room estate inn on the east edge of Stockbridge — main house, cottage house, and barn — with a pool, bar, and fitness center. The architecture is 1906 Gilded Age and the renovation didn't try to modernize it out of existence. A short walk to the Norman Rockwell Museum. The scale keeps it personal in a way the larger Berkshires properties cannot.

West Stockbridge · Inn

A suite-style inn in the village of West Stockbridge — a small, genuinely pleasant town that serves as a quieter alternative to Stockbridge and Lenox. Full kitchens in every suite, a fire pit, and wine and snacks included. Five minutes from the Tanglewood main gate. Original artworks by Berkshire artists throughout. The right answer for anyone wanting proximity to the big-ticket cultural draws without the big-ticket prices.

Housatonic · Inn / B&B

An 1825 house in Housatonic run by former managers of top-tier New York restaurants — which means the hospitality is unusually polished for the price point and the breakfast is taken seriously. Five rooms, Brooklinen bedding, MALIN+GOETZ bath products, Crosley record players, and the kind of personalized attention that a five-room property can give and a fifty-room property cannot.

New Marlborough · Inn

Built in 1760 as a stagecoach stop, now the centerpiece of the historic village of New Marlborough. Eleven rooms with working fireplaces, antique furnishings, and claw-foot tubs. The restaurant — lit entirely by candlelight, no electric light in the dining room — is what brings people here who aren't staying the night. Chef/owner Peter Platt's seasonal menu has been earning serious attention for decades. Yankee's No. 1 Historic Inn in New England.

New Marlborough · Inn / Farm

A working farm property in New Marlborough — Norman and Dutch-style barns on 50 acres, with stalls, hay, and livestock alongside rooms with exposed beams and stone fireplaces. Dog-friendly. The farm is genuinely operating, not decorative. This is the Berkshires' answer to the agri-tourism model: a real property with real animals where you also get a comfortable room and a good breakfast.

Sheffield · Inn / B&B

A five-room B&B in Sheffield — one of the quieter and more genuinely rural towns in southern Berkshire County. Cooked-to-order breakfast on weekends, a fireplace in the lobby, and a location near Bartholomew's Cobble and the Appalachian Trail. Less discovered than the Lenox–Stockbridge corridor, with a corresponding price. The kind of property where the owner remembers you.

Pittsfield · Hotel

A boutique hotel in the center of Pittsfield — the Berkshires' largest city — converted from a 19th-century building on North Street. Art gallery on the ground floor, restaurant, and a location that positions it as the practical midpoint between North County and South County. Pittsfield has a genuine arts scene anchored by Barrington Stage Company and the Colonial Theatre, and Hotel on North is the best way to be inside it.

Adams · Lodge

A 1930s Civilian Conservation Corps stone-and-timber lodge at the 3,491-foot summit of Mount Greylock — the highest point in Massachusetts. Accessible by road or by through-hiking the Appalachian Trail. Private rooms and bunk rooms. Fieldstone fireplaces, arts-and-crafts furnishings, and views that justify the elevation. A Yankee Editors' Pick for Best Inn Landscape. One of the few places in New England where the inn itself is the destination, not an accessory to it.

Lee · Inn / B&B

An eleven-suite inn on six landscaped acres in Lee — all suites have private baths, fireplaces, and spa tubs. Heated swimming pool. Adjacent to the Greenock Country Club's public golf course and clay tennis courts. Ten minutes from Tanglewood. The kind of refined B&B that has accumulated a loyal following quietly, without the marketing overhead of its Lenox neighbors.

Lee · Inn / B&B

An 1824 Federal-style inn on the edge of Lee — five rooms, each individually decorated with period antiques and fireplaces. Intimate, personal, and priced to reflect neither the Lenox premium nor the national brand overhead. A short drive to Tanglewood, Stockbridge, and the Berkshires' cultural core. The kind of inn that operates on word of mouth because it doesn't need anything else.

Lenox · Inn / B&B

A three-room inn and two cottages on a working farm in Lenox — Kripalu-adjacent, quiet, and operating at a scale where the owners know every guest by name. The property has an organic garden, a pond, and direct access to walking trails. One of the smallest and most personal lodging options in the Berkshires, which is both the limitation and the appeal.

Lee · Inn

An 1817 inn on Main Street in Lee — the town between Stockbridge and Lenox that is often overlooked in favor of its famous neighbors. Eleven rooms, a tavern and dining room, and the kind of Main Street location that puts everything in walking distance. Lee has a strong local restaurant scene and Laurel Lake is minutes away. The inn is the right size to know it.

Lenox · Inn / B&B

An 1806 Federal mansion in the heart of Lenox village — eleven rooms, fireplaces, antiques, and the walkable Church Street restaurant scene right outside. One of Lenox's oldest operating inns, and one of the few that places the guest inside the village rather than on its edge. The Berkshires' cultural offerings — Tanglewood, Jacob's Pillow, The Mount — are all within a short drive.