Great Barrington Guest Houses

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Guest Houses in Great Barrington

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

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

9 Academy

9 Academy St, Salisbury, CT

$494

per night

May 15 - May 16

Located in Salisbury, 9 Academy is a 1-minute drive from Harney and Sons Tea Tasting Room and 5 minutes from Mount Riga State Park.

The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

$115

per night

May 15 - May 16

Located in North Granby, this guesthouse is in a rural location, within a 15-minute drive of Lost Acres Vineyard and McLean Game Refuge.

Sweet Dreams Retreat

With a stay at this guesthouse in Sandisfield, you'll be in the mountains, and 8.9 mi (14.3 km) from Questing and 9.1 mi (14.7 km) from Dry Hill.

Hudson valley and The Berkshires Cottage

$93

per night

May 20 - May 21

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.

Renovated Private Guest House by Evergreen Home

With a stay at this guesthouse in Great Barrington, you'll be within a 10-minute drive of Housatonic River and Lake Mansfield Park.

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 Lake Taghkanic State Park.

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.

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 October Mountain State Forest.

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.

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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.