Book Guest Houses in Stockbridge, MA

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Top Guest Houses in Stockbridge

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$94 nightly

$105 total

Jan 4 - Jan 5

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

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$188 nightly

$210 total

Jan 4 - Jan 5

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

$315 nightly

$320 total

Jan 5 - Jan 6

Total with taxes and fees

A garden is available at this guesthouse.

Pet friendly

Free WiFi

Renovated Private Guest House by Evergreen Home

Great Barrington MA

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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

1805 House Bed and Breakfast

775 Snydertown Road Craryville NY

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This guesthouse features free self parking and a terrace. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

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.

Hot Tub

Parking included

Cliffwood Cottage by Evergreen Home

Lenox MA

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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 Stockbridge

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA

$414 nightly

$462 total

Jan 18 - Jan 19

Total with taxes and fees

9.2/10 Wonderful! (85 reviews)

Stockbridge Guest Houses essential information

Accommodation	10 Guest Houses
Lowest Price	$105
Highest Price	$462
Popular accommodation	The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Dewey, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, 1805 House Bed and Breakfast , Chestnut Lodge, Cliffwood Cottage by Evergreen Home, Vanderbilt Lakeside