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

$119 nightly

$133 total

Jun 15 - Jun 16

Total includes 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!!

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This vacation home includes a garden and barbecue grills.

Kitchen

Free WiFi

The Dewey

7 Hubbard Street, Lenox, MA

$159 nightly

$178 total

Jun 16 - Jun 17

Total includes 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

Hudson valley and The Berkshires Cottage

$313 nightly

$316 total

Jun 11 - Jun 12

Total includes 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

Guest House Sanctuary by Evergreen Home

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

Free WiFi

Parking available

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

Cliffwood Cottage by Evergreen Home

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This guesthouse features laundry facilities.

Free WiFi

Air conditioning

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

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.

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.

Top hotels in Stockbridge

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

$120 nightly

$134 total

Jun 17 - Jun 18

Total includes taxes and fees

9/10 Wonderful! (1,003 reviews)

Stockbridge Guest Houses essential information

Accommodation	9 Guest Houses
Lowest Price	$104
Highest Price	$316
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, Guest House Sanctuary by Evergreen Home, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, 1805 House Bed and Breakfast , Vanderbilt Lakeside, Chestnut Lodge