Search Guest Houses in The Berkshires from CA $158

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Aug 22 - Aug 24
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Browse Select The Berkshires Guest Houses

The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (321)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is CA $240
CA $268 total
includes taxes & fees
Sep 10 - Sep 11
The Dewey
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (301)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is CA $158
CA $177 total
includes taxes & fees
Sep 1 - Sep 2
The Central Downtown Inn & Suites
The Revival House
Romantic Room, 1 King Bed (Room 4)

The Revival House

3.0 star property
9.4 out of 10, Exceptional, (10)
"Self check in was easy. Rooms were spacious and clean. Great place."
The price is CA $248
CA $277 total
includes taxes & fees
Aug 17 - Aug 18
The Revival House
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (254)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
Berkshire Village Carriage House - Super Private!!
Renovated Private Guest House by Evergreen Home
Outdoor dining

Renovated Private Guest House by Evergreen Home

10.0 out of 10, Exceptional, (9)
"Great stay. Cute spot!"
Renovated Private Guest House by Evergreen Home
Jacob's Tanglewood Ranch
Dishwasher

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Cliffwood Cottage by Evergreen Home
Interior

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
Chestnut Lodge
Property grounds

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.
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Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"..."
adriana 1-night trip
Posted 17 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG