Pittsfield Guest Houses

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Guest Houses in Pittsfield

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

$125

includes taxes & fees

$112 per night

Mar 16 - Mar 17

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

Hudson valley and The Berkshires Cottage

$294

includes taxes & fees

$294 per night

Mar 23 - Mar 24

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

Located in Great Barrington, this guesthouse is in a rural location, within a 10-minute drive of Housatonic River and Lake Mansfield Park.

Guest House Sanctuary by Evergreen Home

Located in Becket, this guesthouse is a 5-minute drive from Pyramid Lake and 5 minutes from Jacob's Pillow.

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.

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.

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.

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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.