Top Guest Houses in Hampden County in 2026

A calm lake surrounded by dense forest and a clear sky.

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Our top choices for Hampden County guest houses

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

1. The Central Downtown Inn & Suites

Pittsfield

Debra

Rp1.961.714 total

includes taxes & fees

18 Nov - 19 Nov

A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

2. Hideaway Inn Lenox

Lenox

Barbara

Rp2.259.556 total

includes taxes & fees

2 Dec - 3 Dec

A two-story white house with dark shutters, a stone wall, and a front door with an American flag.

3. Spring Hill Inn

Storrs

Jack

Rp4.735.856 total

includes taxes & fees

14 Nov - 15 Nov

A stainless steel refrigerator with a digital display showing the time and date, a microwave above it, and a kettle on the stove.

4. Upscaled Home in a Quiet Neighborhood

Forest Park

Anonymous traveller

Rp9.520.028 total

includes taxes & fees

20 Nov - 21 Nov

A spacious room with a large wooden floor, a patterned rug, a sofa, and a dining table with chairs.

5. The Dewey

Lenox

Thea

A white two-story building with a central entrance, columns, and an American flag.

6. Sturbridge Country Inn

Fiskdale

Christine

Rp5.043.813 total

includes taxes & fees

19 Nov - 20 Nov

A bedroom with a bed, a dresser, and a nightstand.

7. Cheney Bros Hill Top Mansion

Manchester

Marc

A room with large windows, wooden beams, and a bed with floral pillows.

8. Chestnut Lodge

Lee

"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...

Priya