Book Guest Houses in The Berkshires, MA

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Top Guest Houses in The Berkshires

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
$104 nightly
The price is $116 total per night
$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

The Dewey

3.5 out of 5
7 Hubbard Street, Lenox, MA
$185 nightly
The price is $207 total per night
$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
The Revival House

The Revival House

3 out of 5
17 Commercial St, Adams, MA
Free Cancellation
Reserve now, pay when you stay
$168 nightly
The price is $188 total per night
$188 total
Oct 8 - Oct 9
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.
Breakfast included
Parking included
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

$205 nightly
The price is $229 total per night
$229 total
Oct 28 - Oct 29
Total with taxes and fees
This vacation home includes a garden and barbecue grills.
Kitchen
Free WiFi
Renovated Private Guest House by Evergreen Home

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
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
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

Chestnut Lodge

3.5 out of 5
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

Cliffwood Cottage by Evergreen Home

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This guesthouse features laundry facilities.
Free WiFi
Air conditioning
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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 The Berkshires

The Williams Inn

The Williams Inn

101 Spring Street, Williamstown, MA
$199 nightly
The price is $223 total per night from Nov 3 to Nov 4
$223 total
Nov 3 - Nov 4
Total with taxes and fees
9.6/10 Exceptional! (508 reviews)

The Berkshires Guest Houses essential information

Accommodation
8 Guest Houses
Lowest Price
$96
Highest Price
$229
Popular accommodation
The Central Downtown Inn & Suites, The Dewey, The Revival House, Berkshire Village Carriage House - Super Private!!, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home

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