Great Barrington Guest Houses

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Guest Houses in Great Barrington

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$102 nightly

$114 total

Feb 24 - Feb 25

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

$200 nightly

$223 total

Mar 9 - Mar 10

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

$478 nightly

$550 total

Mar 26 - Mar 27

Total with taxes and fees

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

$217 nightly

$246 total

Feb 24 - Feb 25

Total with taxes and fees

Located in North Granby, this guesthouse is in a rural location, within a 5-minute drive of Granby Land Trust Preserves and Hartland Recreation Area.

Hudson valley and The Berkshires Cottage

Hillsdale NY

$344 nightly

$349 total

Mar 26 - Mar 27

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.

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.

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.

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.