Book Guest Houses in Pittsfield, MA

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Top Guest Houses in Pittsfield

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.

Hudson valley and The Berkshires Cottage

$98

per night

May 29 - May 30

Stay at this guesthouse in Hillsdale. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Catamount Aerial Adventure Park and Art et Industrie are located nearby.

Renovated Private Guest House by Evergreen Home

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This guesthouse includes a garden and barbecue grills.

Jacob's Tanglewood Ranch

560 Stockbridge Rd, Lee, MA

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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and a communal living room are also on offer.

Chestnut Lodge

75 Chestnut Street, Lee, MA

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A spa tub is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A terrace and a picnic area are also provided.

Vanderbilt Lakeside

161 Main St, Philmont, NY

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This guesthouse features free WiFi in public areas, wedding services, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a garden, and a communal living room are also on offer.

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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.

Top hotels in Pittsfield

Berkshire Inn

150 W Housatonic St, Pittsfield, MA

$72

per night

May 19 - May 20

7.6/10 Good! (656 reviews)

Pittsfield Guest Houses essential information

Accommodation	7 Guest Houses
Lowest Price	$72
Highest Price	$166
Popular accommodation	The Central Downtown Inn & Suites, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge, Vanderbilt Lakeside