Book Guest Houses in Pittsfield, MA

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Top Guest Houses in Pittsfield

Hideaway Inn Lenox

11 Old Stockbridge Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$186 nightly

$208 total

Sep 27 - Sep 28

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and picnic area. A communal living room, a library, and a virtual front desk are also on offer.

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$99 nightly

$111 total

Aug 30 - Aug 31

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 Revival House

17 Commercial St Adams MA

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$170 total

Sep 6 - Sep 7

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.

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$189 nightly

$211 total

Aug 31 - Sep 1

Total with taxes and fees

This guesthouse includes a garden and barbecue grills.

Free WiFi

Air conditioning

The Dewey

7 Hubbard Street Lenox MA

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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

Hudson valley and The Berkshires Cottage

Hillsdale NY

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A garden is available at this guesthouse.

Renovated Private Guest House by Evergreen Home

Great Barrington MA

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

Cliffwood Cottage by Evergreen Home

Lenox MA

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This guesthouse features laundry facilities.

Free WiFi

Air conditioning

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.

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

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.

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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

Hotel On North

297 North Street Pittsfield MA

$179 nightly

$200 total

Sep 7 - Sep 8

Total with taxes and fees

9.6/10 Exceptional! (903 reviews)

Pittsfield Guest Houses essential information

Accommodation	11 Guest Houses
Lowest Price	$64
Highest Price	$211
Popular accommodation	Hideaway Inn Lenox, The Central Downtown Inn & Suites, The Revival House, Berkshire Village Carriage House - Super Private!!, The Dewey, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Cliffwood Cottage by Evergreen Home, Jacob's Tanglewood Ranch, Vanderbilt Lakeside, Chestnut Lodge