The Berkshires Travel Guide
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21 Hotels

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21 Hotels

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1

Blantyre

$$$$ | 16 Blantyre Rd.

Modeled after a castle in Scotland, the 1902 manor house debuted a multi-million dollar renovation in early 20... Read More

B&B/Inn · Luxurious Retreat · Sophisticated · Countryside


2

Cranwell Resort, Spa, and Golf Club

$$$$ | 55 Lee Rd.

This 380-acre resort features a mansion built in 1894, carriage houses, and grounds designed by Frederick Law... Read More

Resort · Luxurious Retreat · Quiet · Countryside · Family


3

Gateways Inn and Restaurant

$$$ | 51 Walker St.

The cozy B&B was built in 1912 as the summer cottage for Harley Procter of the Procter and Gamble empire. Read More

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


4

The Inn at Stockbridge

$$$ | 30 East St.

Built in 1906 as a Georgian Revival summer house, the B&B is a cozy hideaway with homecooked meals and stunnin... Read More

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


5

The Red Lion Inn

$$$ | 30 Main St.

An inn since 1773, the Red Lion has hosted presidents and senators, and now is draw for tourists and families. Read More

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


6

Applegate Inn

$$ | 279 W. Park St.

This intimate 1925 Georgian Revival mansion overlooks 6 acres of lush lawns and apple trees. Read More

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


7

Devonfield Inn

$$ | 85 Stockbridge Rd.

For hillside views and ample amenities, check into the restored Federal-style house turned cozy B&B. Read More

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


8

Orchards Hotel

$$ | 222 Adams Rd.

While it's short on unique flavor, the hotel provides spacious and comfortable rooms and updated bathrooms. Read More

Hotel · Trendy · Practical Base · Quiet · Central


9

Porches Inn

$$ | 231 River St.

Six Victorian rowhouses, originally built as accommodations for mill workers, are transformed into a boutique... Read More

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


10

The Barrington

$$ | 281 Main St., 3rd fl.

Stay in an urban retreat in the heart of the Berkshires. Read More

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


11

Topia Inn

$$ | 10 Pleasant St.

Slip into an aromatherapy tub and savor homemade, organic breakfast at this colorful inn in the heart of the B... Read More

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


12

Brook Farm Inn

$ | 15 Hawthorne St.

Unwind at a restored Victorian home with afternoon tea and homemade scones. Read More

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


13

Chambery Inn

$ | 199 Main St.

Sleep in rooms that retain original blackboards in this converted 19th-century country schoolhouse turned B&B. Read More

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


14

Country Inn at Jiminy Peak

$ | 37 Corey Rd.

Stone fireplaces in the lobby, apres-ski drinks, and heated pool lend this hotel a ski-lodge atmosphere year-r... Read More

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


15

Guest House at Field Farm

$ | 554 Sloan Rd.

Live out your mid-century modern dreams while enjoying breathtaking views of Mt. Greylock. Read More

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


16

River Bend Farm

$ | 643 Simonds Rd.

The 1770 Georgian Colonial takes guests back to a different era with original architecture and rustic bathroom... Read More

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


17

Wainright Inn

$ | 518 S. Main St.

Sip iced tea on the wraparound porch or lounge by the fire in this stately Victorian built in 1766. Read More

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


18

Whistler's Inn

$ | 5 Greenwood St.

Delight in period details and an atmosphere attracting artists, musicians and curious travelers from around th... 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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