Stockbridge Guest Houses

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Guest Houses in Stockbridge

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$85 nightly

$95 total

Dec 7 - Dec 8

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

$189 nightly

$211 total

Dec 8 - Dec 9

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 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

Hudson valley and The Berkshires Cottage

Hillsdale NY

$305 nightly

$310 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this guesthouse in Hillsdale, you'll be within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Hillsdale Town Hall.

Pet friendly

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

1805 House Bed and Breakfast

775 Snydertown Road Craryville NY

Located in Craryville, 1805 House Bed and Breakfast is in a rural location, within a 15-minute drive of Claverack Library and Stoddard Corner.

Breakfast included

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.

Hot Tub

Parking included

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.

Free WiFi

Air conditioning

Vanderbilt Lakeside

161 Main St Philmont NY

Located in Philmont, Vanderbilt Lakeside is on a lake, within a 15-minute drive of High Falls Trail and Claverack Library.

Breakfast included

Parking included

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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.