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.

Pet friendly

Parking included

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.

Pet friendly

Air conditioning

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.

Pet friendly

Free WiFi

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.

Free WiFi

Parking available

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

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.

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.

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.