Book Guest Houses in Great Barrington, MA

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Top Guest Houses in Great Barrington

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$107 nightly

$120 total

May 31 - Jun 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.

Berkshire Village Carriage House - Super Private!!

Lanesborough MA

$188 nightly

$210 total

May 31 - Jun 1

Total with taxes and fees

This guesthouse includes a garden and barbecue grills.

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

Granby CT

$220 nightly

$249 total

May 31 - Jun 1

Total with taxes and fees

A garden is available at this guesthouse.

9 Academy

9 Academy St Salisbury CT

$500 nightly

$575 total

Jun 9 - Jun 10

Total with taxes and fees

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

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.

Hudson valley and The Berkshires Cottage

Hillsdale NY

$329 nightly

$334 total

Jun 4 - Jun 5

Total with taxes and fees

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.

The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

Granby CT

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This guesthouse includes a garden and laundry facilities.

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.

Cliffwood Cottage by Evergreen Home

Lenox MA

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This guesthouse features laundry facilities.

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.

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.

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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 Great Barrington

Prospect Berkshires

50 Prospect Lake Rd Egremont MA

$337 nightly

$376 total

May 31 - Jun 1

Total with taxes and fees

9.8/10 Exceptional! (29 reviews)

Great Barrington Guest Houses essential information

Accommodation	13 Guest Houses
Lowest Price	$85
Highest Price	$575
Popular accommodation	The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, 9 Academy , The Dewey, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge, 1805 House Bed and Breakfast