Top Guest Houses in Hampshire County in 2025

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Top Cities in Hampshire County

Featured Guest Houses in Hampshire County

"excellent stay!! The Dewey is a cozy getaway location!"

CA $262 total

includes taxes & fees

Sep 1 - Sep 2

"Friendly staff, clean and perfect for a trip with the pups! "

CA $177 total

includes taxes & fees

Sep 1 - Sep 2

"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. "

CA $277 total

includes taxes & fees

Aug 4 - Aug 5

"Lovely Inn and very responsive and approachable staff. "

CA $198 total

includes taxes & fees

Aug 4 - Aug 5

"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. "

CA $542 total

includes taxes & fees

Aug 14 - Aug 15

CA $588 total

includes taxes & fees

Aug 8 - Aug 9

"Enjoyed staying"

CA $365 total

includes taxes & fees

Aug 12 - Aug 13

"Great place. Quiet, clean and spacious - thank you so much "

CA $239 total

includes taxes & fees

Aug 24 - Aug 25

"Great stay. Cute spot!"

"A truly exceptional pleasure in the middle of nowhere. Peaceful and comfortable. Good for quiet reflection, long walks, or sitting around with family or friends. No amenities and the local area means a 15 to 20 minute drive, but hey, you stay here for the peacefulness of the lodge and sounds."

"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...

"Angel's Rest is sooo peaceful. We had a delicious and super healthy breakfast in the breakfast nook, surrounded by lovely plants and a small fountain, looking out over the rolling hills of Western Mass. The fall colors were nice. "