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.

18 Matching Hotels

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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. 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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6. 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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7. 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

8. Porches Inn

$$ | 231 River St., North Adams, Massachusetts, 01247, USA

Dilapidated mill-workers' houses dating to the 1890s have been restored and connected with one long porch—comp... Read More

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9. 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

10. The Barrington

$$ | 281 Main St., 3rd fl., Great Barrington, Massachusetts, 01230, USA

As a third-floor bed-and-breakfast above retail frontage, the Barrington may lack the exterior aesthetic appea... Read More

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