The Berkshires Guest Houses

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Guest Houses in The Berkshires

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$85 nightly

$95 total

Dec 15 - Dec 16

Total with taxes and fees

Located in Pittsfield, The Central Downtown Inn & Suites is a 1-minute drive from Berkshire Museum and 7 minutes from Bousquet Ski Area.

Pet friendly

Parking included

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$187 nightly

$209 total

Dec 13 - Dec 14

Total with taxes and fees

Located in Lanesborough, this guesthouse is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.

Free WiFi

Air conditioning

The Revival House

17 Commercial St Adams MA

$150 nightly

$168 total

Dec 14 - Dec 15

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at The Revival House in Adams, you'll be a 5-minute walk from Adams Theater and 10 minutes by foot from Berkshire Scenic Railway Museum.

Breakfast included

Parking included

The Dewey

7 Hubbard Street Lenox MA

With a stay at The Dewey in Lenox, you'll be in the suburbs, within a 5-minute drive of Tanglewood Music Center and The Bookstore.

Parking included

Free WiFi

Renovated Private Guest House by Evergreen Home

Great Barrington MA

Located in Great Barrington, this guesthouse is in a rural location, within a 10-minute drive of Monument Mountain and Housatonic River.

Pet friendly

Free WiFi

Jacob's Tanglewood Ranch

560 Stockbridge Rd Lee MA

With a stay at Jacob's Tanglewood Ranch in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

Pet friendly

Parking included

Chestnut Lodge

75 Chestnut Street Lee MA

With a stay at Chestnut Lodge in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.

Cliffwood Cottage by Evergreen Home

Lenox MA

With a stay at this guesthouse, you'll be centrally located in Lenox, within a 5-minute drive of Tanglewood Music Center and The Bookstore.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.