Romantic Getaways in the Berkshires

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.

Lenox · Hotel / Motel

A 1970s roadside motel on the north edge of Lenox, gutted and redesigned by the Life House hospitality group. The transformation is complete: the lobby and cocktail bar are seriously designed, with plush eclectic armchairs and floor-to-ceiling bookshelves. Warm, not kitschy. The kind of conversion that makes you reconsider what a motel can be without overselling the premise.

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.

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.

Egremont · Inn / Farm

A working sheep farm and inn in the quiet hamlet of Egremont, near the New York border and the Catamount ski area. Eight rooms across an 18th-century farmhouse. Homemade breakfasts using farm eggs. The setting is genuinely rural in the southern Berkshires — no boutique signaling, no design moment. The kind of inn where people return the same week every year and the owners know why.

Richmond · Inn / B&B

A classic New England inn on 27 acres in Richmond — quiet, unhurried, with horses on the property and a breakfast program worth the morning. Equestrian setting with riding available. Between Pittsfield and the Connecticut border, well-positioned for anyone exploring the central Berkshires without paying the Lenox premium. The guests who find this place tend to come back.

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.

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.

Lee · Inn

A small inn directly on Laurel Lake in Lee — lake swimming, kayaking, and a porch view that the properties in Lenox and Stockbridge can't offer. The scale is right: the number of rooms means the lake doesn't feel crowded. A short drive to Tanglewood and the Stockbridge Bowl. For people whose ideal Berkshires stay involves a swim at the end of the afternoon.