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

$104 nightly

$116 total

Oct 31 - Nov 1

Total with taxes and fees

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.

Pet friendly

Parking included

The Dewey

7 Hubbard Street, Lenox, MA

$185 nightly

$207 total

Oct 29 - Oct 30

Total with taxes and fees

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

Parking included

Free WiFi

The Revival House

17 Commercial St, Adams, MA

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$188 total

Oct 8 - Oct 9

Total with taxes and fees

This guesthouse features free WiFi in public areas, a virtual front desk, and free self parking. Enjoy the free self-serve breakfast each morning. A communal living room is also provided.

Breakfast included

Parking included

Berkshire Village Carriage House - Super Private!!

$205 nightly

$229 total

Oct 28 - Oct 29

Total with taxes and fees

This vacation home includes a garden and barbecue grills.

Kitchen

Free WiFi

Hudson valley and The Berkshires Cottage

$310 nightly

$315 total

Oct 6 - Oct 7

Total with taxes and fees

This guesthouse includes a garden and laundry facilities.

Pet friendly

Free WiFi

Renovated Private Guest House by Evergreen Home

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This guesthouse features a garden, laundry facilities, and barbecue grills.

Pet friendly

Free WiFi

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.

Pet friendly

Parking included

Chestnut Lodge

75 Chestnut Street, Lee, MA

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A hot 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.

Hot Tub

Parking included

Cliffwood Cottage by Evergreen Home

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This guesthouse features laundry facilities.

Free WiFi

Air conditioning

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.

Breakfast included

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.

Top hotels in Pittsfield

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

1055 South Street, Pittsfield, MA

$144 nightly

$160 total

Nov 2 - Nov 3

Total with taxes and fees

9.4/10 Exceptional! (48 reviews)

Pittsfield Guest Houses essential information

Accommodation	10 Guest Houses
Lowest Price	$84
Highest Price	$315
Popular accommodation	The Central Downtown Inn & Suites, The Dewey, The Revival House, Berkshire Village Carriage House - Super Private!!, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home, Vanderbilt Lakeside