21 Hotels

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1

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

B&B/Inn · Luxurious Retreat · Sophisticated · Countryside · Fodor's Splurge


2

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

Resort · Luxurious Retreat · Quiet · Countryside · Fodor's Splurge · Family


3

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

B&B/Inn · Trendy · Casual Chic · Intimate · Central · Fodor's Choice


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

B&B/Inn · Historical · Design · Intimate · Countryside · Fodor's Choice


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

B&B/Inn · Historical · Local Flavor · Casual · Central · Fodor's Choice


6

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

B&B/Inn · Romantic · Luxurious Retreat · Quiet · Countryside


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

B&B/Inn · Historical · Luxurious Retreat · Quiet · Countryside · Fodor's Choice


8

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

Hotel · Trendy · Practical Base · Quiet · Central


9

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

B&B/Inn · Local Flavor · Intimate · Central · Fodor's Splurge · Fodor's Choice


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

New · Practical Base · Central · B&B/Inn · Casual


11

Topia Inn

$$ | 10 Pleasant St., Adams, Massachusetts, 01220, USA

Innkeepers Nana Simopoulos and Caryn Heilman have transformed a derelict downtown building into an eco-friendl… Read More

B&B/Inn · Green · Design · Quiet · Central


12

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

B&B/Inn · Romantic · Local Flavor · Intimate · Countryside


13

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

B&B/Inn · Historical · Local Flavor · Quiet · Central


14

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

Resort · Views · Practical Base · Casual · Near the mountain


15

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

B&B/Inn · Views · Design · Quiet · Countryside


16

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

B&B/Inn · Historical · Local Flavor · Quiet · Central


17

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

B&B/Inn · Historical · Design · Casual · Central


18

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

B&B/Inn · Historical · Luxurious Retreat · Intimate · Countryside


19

Harrison House

$$ | 174 Main St., Lenox, Massachusetts, 01240, USA

An inviting white Victorian house with a sweeping wraparound porch across from Lenox's White Church on the Hil… Read More

B&B/Inn · Service · Design · Quiet · Central


20

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

B&B/Inn · Historical · Practical Base · Quiet · Countryside

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