The Berkshires Hotels

Our travel experts have picked the best hotels in The Berkshires so you can be sure you’re staying in top accommodations.

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1. Chambery Inn

$ | 199 Main St., Lenox, Massachusetts, 01238, USA

A converted 19th-century country schoolhouse houses these unique accommodations in downtown Lee. Large guest r... Read More

2. Devonfield Inn

$$ | 85 Stockbridge Rd., Lee, Massachusetts, 01238, USA

Occupying a grand Federal house, the Devonfield sits atop a birch-shaded hillside overlooking 32 acres of roll... Read More

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3. River Bend Farm

$ | 643 Simonds Rd., Williamstown, Massachusetts, 02167, USA

Listed on the National Register of Historic Places, this 1770 Georgian Colonial is neither on a river nor is i... Read More

4. The Inn at Stockbridge

$$$ | 30 East St., Stockbridge, Massachusetts, 01262, USA

Antique furnishings and feather comforters are among the accents in the guest rooms of this 1906 Georgian Revi... Read More

5. The Red Lion Inn

$$$ | 30 Main St., Stockbridge, Massachusetts, 01262, USA

An inn since 1773, the Red Lion has hosted presidents, senators, and other celebrities, these days between a l... Read More

6. Wainright Inn

$ | 518 S. Main St., Great Barrington, Massachusetts, 01230, USA

Built in 1766 as the Troy Tavern & Inn, this well-run lodging has wraparound porches on two levels; the gr... Read More

7. Whistler's Inn

$ | 5 Greenwood St., Lenox, Massachusetts, 01240, USA

Antiques adorn the parlor of this 1870s Tudor-style mansion, alongside items picked up on the innkeepers' worl... Read More

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8. Historic Merrell Inn

$$ | 1565 Pleasant St., off Hwy. 102, South Lee, Massachusetts, 01260, USA

Built in 1794 as a private residence and later converted to a stagecoach stop, this meticulously maintained in... Read More

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