Great Barrington Guest Houses

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Guest Houses in Great Barrington

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$94 nightly

$105 total

Jan 25 - Jan 26

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.

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$186 nightly

$208 total

Jan 20 - Jan 21

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.

9 Academy

9 Academy St Salisbury CT

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 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.

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

Granby CT

$237 nightly

$269 total

Jan 19 - Jan 20

Total with taxes and fees

Located in North Granby, this guesthouse is in a rural location, within a 10-minute drive of Hartland Town Hall and Enders State Forest.

Air conditioning

Parking available

Hudson valley and The Berkshires Cottage

Hillsdale NY

$342 nightly

$347 total

Jan 21 - Jan 22

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.

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.

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 Columbia-Greene Hospital Foundation.

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.

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.