Book Guest Houses in The Berkshires

Start date: Check-in selected.
To Date
End date: Check-out

Wander Wisely with exceptional service, 24/7 support

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

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
The price is CA $127 per night
CA $127
CA $142 total
Feb 15 - Feb 16
includes taxes & fees
Stay at this guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located nearby.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
The price is CA $184 per night
CA $184
CA $286 total
Feb 1 - Feb 2
includes taxes & fees
Stay at this guesthouse in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Crane Museum of Papermaking are located nearby.
The Revival House

The Revival House

3 out of 5
17 Commercial St Adams MA
Free cancellation
Reserve now, pay when you stay
The price is CA $204 per night
CA $204
CA $228 total
Feb 8 - Feb 9
includes taxes & fees
Book a stay at this 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
The Dewey

The Dewey

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

Renovated Private Guest House by Evergreen Home

Great Barrington MA
Get rates
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
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
560 Stockbridge Rd Lee MA
Get rates
Stay at this guesthouse in Lee. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Greenock Country Club and Berkshire Theatre Festival are located nearby.
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street Lee MA
Get rates
Stay at this guesthouse in Lee. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Goose Pond Reservation and Lee Premium Outlets are located nearby.
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

Lenox MA
Get rates
Stay at this guesthouse in Lenox. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions The Bookstore and Lenox Library are located nearby.
Don't see what you're looking for?
See all available properties in The Berkshires
View all properties
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 Williams Inn

The Williams Inn

101 Spring Street Williamstown MA
The price is CA $249 per night from Mar 3 to Mar 4
CA $249
CA $279 total
Mar 3 - Mar 4
includes taxes & fees
9.6/10 Exceptional! (571 reviews)

The Berkshires Guest Houses essential information

Accommodation
8 Guest Houses
Lowest Price
CA $133
Highest Price
CA $286
Popular accommodation
The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Revival House, The Dewey, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home

Explore more Guest Houses

More places to stay in The Berkshires