Book Guest Houses in Great Barrington, MA

Top Guest Houses in Great Barrington

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

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

9 Academy

9 Academy St, Salisbury, CT

$494 nightly

$568 total

Oct 6 - Oct 7

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.

Parking included

Free WiFi

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

$233 nightly

$265 total

Oct 22 - Oct 23

Total with taxes and fees

This guesthouse features limo/town car service, a garden, and concierge services.

Air conditioning

Parking available

Hudson valley and The Berkshires Cottage

$308 nightly

$313 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

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

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.

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 Great Barrington

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd, Great Barrington, MA

$143 nightly

$160 total

Nov 2 - Nov 3

Total with taxes and fees

9.2/10 Wonderful! (738 reviews)

Great Barrington Guest Houses essential information

Accommodation	12 Guest Houses
Lowest Price	$74
Highest Price	$568
Popular accommodation	The Central Downtown Inn & Suites, The Dewey, Berkshire Village Carriage House - Super Private!!, 9 Academy , A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, 1805 House Bed and Breakfast , Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home, Vanderbilt Lakeside