Search Guest Houses in The Berkshires

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Featured Guest Houses in The Berkshires

The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (318)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is P10,528
P11,760 total
includes taxes & fees
Sep 2 - Sep 3
The Dewey
The Central Downtown Inn & Suites
Compact kitchen with modern design, featuring white and wood cabinetry, refrigerator, coffee maker, and toaster.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (299)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is P6,689
P7,472 total
includes taxes & fees
Sep 1 - Sep 2
The Central Downtown Inn & Suites
The Revival House
Cozy living room with a fireplace, dining area, and high ceiling.

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (8)
"Beautifully renovated historical bed and breakfast that offers historical details along with modern touches. Our room was spacious and very clean and common areas are appointed with great attention to detail. "
The price is P10,470
P11,694 total
includes taxes & fees
Aug 5 - Aug 6
The Revival House
Jacob's Tanglewood Ranch
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, and red stove.

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Chestnut Lodge
Escape to a secluded cabin nestled among the trees, offering a peaceful retreat in the heart of nature.

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top The Berkshires Hotel Reviews

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"My stay was perfect. I can't wait to stay there again. "
RICHARD 2-night trip
Posted 21 hours ago
Howard Johnson by Wyndham Lenox