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. Applegate Inn

$$ | 279 W. Park St., Lenox, Massachusetts, 01238, USA

This 1925 Georgian Revival mansion sits at the end of a regal circular drive, overlooking 6 acres of lush lawn... Read More

2. Blantyre

$$$$ | 16 Blantyre Rd., off U.S. 20, Lenox, Massachusetts, 01240, USA

Modeled after a castle in Scotland, this supremely elegant 1902 manor house sits amid nearly 117 acres of mani... Read More

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3. Brook Farm Inn

$ | 15 Hawthorne St., Lenox, Massachusetts, 01240, USA

Tucked away in a wooded glen a short distance from Tanglewood, this 1880s inn often has classical music playin... Read More

4. 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

5. Country Inn at Jiminy Peak

$ | 37 Corey Rd., Hancock, Massachusetts, 01237, USA

Massive stone fireplaces in the lobby and lounge lend this hotel a ski-lodge atmosphere, and the condo-style s... Read More

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6. Cranwell Resort, Spa, and Golf Club

$$$$ | 55 Lee Rd., Rte. 20, Lenox, Massachusetts, 01240, USA

This 380-acre resort is tastefully upscale, as you'll see from the guest rooms in the Mansion; all are furnish... Read More

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7. 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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8. Gateways Inn and Restaurant

$$$ | 51 Walker St., Lenox, Massachusetts, 01240, USA

The 1912 summer cottage of Harley Procter (as in, Procter & Gamble) has had numerous owners during its ten... Read More

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9. Guest House at Field Farm

$ | 554 Sloan Rd., Williamstown, Massachusetts, 02167, USA

Built in 1948, this guesthouse contains a fine collection of art on loan from Williams College and the Whitney... Read More

10. Orchards Hotel

$$ | 222 Adams Rd., Williamstown, Massachusetts, 01267, USA

Although it's near Route 2 and surrounded by parking lots, this thoroughly proper hostelry compensates with a... Read More

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