Great Barrington Guest Houses

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Guest Houses in Great Barrington

Hideaway Inn Lenox

11 Old Stockbridge Rd Lenox MA

$151 nightly

$169 total

Jul 22 - Jul 23

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

When you stay at Hideaway Inn Lenox in Lenox, you'll be near ski lifts, within a 5-minute drive of Shakespeare and Company and Tanglewood Music Center.

Pet friendly

Parking included

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$107 nightly

$120 total

Jul 22 - Jul 23

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

9 Academy

9 Academy St Salisbury CT

$534 nightly

$615 total

Aug 19 - Aug 20

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.

Parking included

Free WiFi

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$240 nightly

$268 total

Jul 22 - Jul 23

Total with taxes and fees

Located in Lanesborough, this guesthouse is in the mountains, a 4-minute drive from Cheshire Reservoir and 6 minutes from Pontoosuc Lake.

Free WiFi

Air conditioning

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

Granby CT

$220 nightly

$249 total

Jul 29 - Jul 30

Total with taxes and fees

Located in North Granby, this guesthouse is in a rural location, within a 5-minute drive of Godard Preserve and Frederick H. Cossitt Library.

Air conditioning

Parking available

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

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

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

Granby CT

Located in North Granby, this guesthouse is in a rural location, within a 15-minute walk of Lost Acres Vineyard and Kendall Stevens Preserve.

Air conditioning

Parking available

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

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

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.

Hot Tub

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.