Find Your Perfect Bed-and-Breakfast | Berkshires Award-Winners

Yankee editors share some of their favorite picks for kicking back at a bed-and-breakfast, Berkshires–style.

By Yankee Staff

Mar 19 2021

Berkshires bed and breakfasts Devonfield

Devonfield Inn, Lee | Berkshires Bed-and-Breakfasts

Photo Credit : Courtesy of Devonfield Inn
There are few better places for a classic New England country escape than western Massachusetts, where some of our favorite Berkshires bed-and-breakfasts await. The region is blessed with both natural attractions — mountains for skiing and hiking, rivers and lakes for swimming and boating (even whitewater rafting) — and world-class cultural attractions, too. Here is where you will find the nation’s largest center for contemporary visual and performing arts, Mass MoCA; the summer home of the Boston Symphony Orchestra, Tanglewood; and the renowned Jacob’s Pillow dance festival. Below are more than a dozen distinctive places to overnight in the Berkshires, all of which have been named a Yankee Best of New England Editors’ Pick for Massachusetts.

Award-Winning Berkshires Bed-and-Breakfasts

Northern Berkshires B&Bs

The Blackinton Manor | North Adams

Local mill owner Sanford Blackinton spared no expense when he built this Italianate Federal mansion in 1832. Its elegance is undiminished today as a country inn that treats guests to three-course gourmet breakfasts, a wine and cheese reception, and a choice of five refined rooms with lovely window views (including the dog-friendly Carriage Room, with easy outdoor access). Among the other amenities are a pool, gardens, and a cozy living room with fireplace.
The Guest House at Field Farm | Bed-and-Breakfasts in the Berkshires
The Guest House at Field Farm, Williamstown | Berkshires Bed-and-Breakfasts
Photo Credit : Jumping Rock/The Trustees of Reservations

The Guest House at Field Farm | Williamstown

Owned by the Trustees of Reservations, this 1948 Bauhaus-inspired private home filled with classic modern furnishings could have easily become a museum. Instead, it’s a six-room guest house, with ample public areas for lounging, great views of Mount Greylock, and a full country breakfast each morning. Four miles of hiking trails are a bonus.
Topia Inn, Adams | Berkshires Bed-and-Breakfasts
Topia Inn, Adams | Berkshires Bed-and-Breakfasts
Photo Credit : Courtesy of the Topia Inn

Topia Inn | Adams

The beauty and comfort of this solar- and biodiesel-powered B&B is proof positive that reducing the carbon footprint of your travels doesn’t require sacrificing luxury. Nine artist-designed rooms, unique in their exotic motifs, have been furnished exclusively with inert and organic materials. Just minutes from Mass MoCA, the Topia Inn is situated at the base of Mount Greylock next to the Ashuwillticook Rail Trail.
Harbour House Inn, Cheshire | Berkshires Bed-and-Breakfasts
Photo Credit : Courtesy of Harbour House Inn

Harbour House Inn | Cheshire

What began in 1793 as a big tavern and farmhouse is now a romantic country manor with six attractive guest rooms over three floors. But its heart is the common space running the full length of the house, from the music room’s baby grand piano right through to the dining room’s table for 12. The owners are longtime Berkshire residents who can point you to all the best local attractions and dining spots.

Central Berkshires B&Bs

The Garden Gables Inn, Lenox | Berkshires Bed-and-Breakfasts
Garden Gables Inn, Lenox | Berkshires Bed-and-Breakfasts
Photo Credit : Courtesy of the Garden Gables Inn

Garden Gables Inn | Lenox

Almost hidden by the trees and landscaping of its five-acre grounds, this posh Berkshires retreat offers 15 rooms and suites, many in the 1780 main house, with several others in two adjoining cottages. Many rooms feature fireplaces; the two suites and several other rooms feature private porches or decks. Homemade cookies and a free wine tasting at nearby Furnace Brook Winery are among the many perks.
The Gateways Inn, Lenox | Berkshires Bed-and-Breakfasts
The Gateways Inn, Lenox | Berkshires Bed-and-Breakfasts
Photo Credit : Courtesy of the Gateways Inn

The Gateways Inn | Lenox

Built as a summer escape for the family of Procter & Gamble heir Harvey Procter in 1912, this mansion has been transformed into a truly memorable bed-and-breakfast inn. Just a mile and a half from Tanglewood, Gateways offers 11 handsome antiques-filled rooms, including some with sleigh beds and fireplaces. The impressive daily breakfast buffet features a hot entree (meat-free but hearty), homemade granola and baked treats, fruit and cheese, and coffee from local favorite Six Depot in West Stockbridge.

Southern Berkshires B&Bs

Wainwright Inn, Great Barrington | Berkshires Bed-and-Breakfasts
Wainwright Inn B&B, Great Barrington | Berkshires Bed-and-Breakfasts
Photo Credit : Courtesy of the Wainwright Inn B&B

Wainwright Inn B&B | Great Barrington

A Great Barrington landmark that dates back to before the American Revolution, this B&B offers nine cozy rooms and suites in the main inn and a carriage house. Several of the rooms have fireplaces, as do the parlors, where the guests congregate; the garden with terrace is another popular hangout. Just down the road from Ski Butternut and convenient to the slopes of Otis Ridge and New York’s Catamount, the Wainwright is a handy home base for skiers, who will even find ski storage provided on-site.

Inn at Sweet Water Farm | Great Barrington

The Berkshires may be full of cozy 19th-century inns, but none offers such an effortless blend of contemporary folk art, luxurious bedding, and gourmet food. The owners’ passion for showcasing the bounty of local producers, with special help from the inn’s own egg-laying hens, results in scrumptious farm-to-table breakfasts.
Devonfield Inn, Lee | Berkshires Bed-and-Breakfasts
Devonfield Inn, Lee | Berkshires Bed-and-Breakfasts
Photo Credit : Courtesy of Devonfield Inn

Devonfield Inn | Lee

Doug Bagnasco and Jim DeBlasi make patrons feel like houseguests in this elegant English country estate, which has 10 individually decorated rooms and suites and a standalone cottage. Enticements include a landscaped pool with mountain views, wood-burning fireplaces and whirlpool baths, candlelight gourmet breakfasts, plus a guest pantry that’s always open and stocked with fresh-baked cookies and other snacks. This post was first published in 2019 and has been updated. 

SEE MORE: Best Outdoor Dining in the Berkshires5 Favorite Outdoor Activities in the BerkshiresBest Cape Cod B&Bs