Book Guest Houses in The Berkshires

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Featured 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
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Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located nearby.
Pet-friendly
Parking included
The Revival House

The Revival House

3 out of 5
17 Commercial St, Adams, MA
Free cancellation
Reserve now, pay when you stay
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Stay at this 3-star business-friendly guesthouse in Adams. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Adams Theater and Berkshire Scenic Railway Museum are located nearby.
Breakfast included
Parking included
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

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Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Crane Museum of Papermaking and Crane Museum of Papermaking are located nearby.
Kitchen
Free WiFi
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street, Lenox, MA
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Stay at this 3.5-star guesthouse in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.
Parking included
Free WiFi
Renovated Private Guest House by Evergreen Home

Renovated Private Guest House by Evergreen Home

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Stay at this guesthouse in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Art et Industrie and Lake Mansfield Park are located nearby.
Pet-friendly
Free WiFi
Guest House Sanctuary by Evergreen Home

Guest House Sanctuary by Evergreen Home

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Stay at this guesthouse in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jacob's Pillow and Pyramid Lake are located nearby.
Free WiFi
Parking available
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
560 Stockbridge Rd, Lee, MA
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Stay at this 3-star guesthouse in Lee. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Tanglewood Music Center and Greenock Country Club are located nearby.
Pet-friendly
Parking included
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

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Stay at this guesthouse in Lenox. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.
Free WiFi
Air conditioning
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street, Lee, MA
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Stay at this 3.5-star guesthouse in Lee. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Goose Pond Reservation and Lee Premium Outlets are located nearby.
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 trending hotels in The Berkshires

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA
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9/10 Wonderful! (1,003 reviews)

The Berkshires Guest Houses essential information

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

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