Top Guest Houses in Hampden County in 2026

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Top Cities in Hampden County

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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

CA $153 total

includes taxes & fees

Nov 17 - Nov 18

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

2. Hideaway Inn Lenox

Lenox

Barbara

CA $168 total

includes taxes & fees

Nov 12 - Nov 13

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

CA $333 total

includes taxes & fees

Nov 16 - Nov 17

A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

4. Berkshire Village Carriage House - Super Private!!

Lanesborough

Mary R.

CA $281 total

includes taxes & fees

Nov 15 - Nov 16

A modern dining area with a glass table, black chairs, and a teal upholstered chair.

5. Upscaled Home in a Quiet Neighborhood

Forest Park

Anonymous traveller

CA $727 total

includes taxes & fees

Nov 15 - Nov 16

A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.

6. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

Granby

Tiffany N.

CA $335 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with white cabinetry, a built-in oven, a microwave, and a sink. There is a window with a view of the outside, and a door leading to another room.

7. Hill Ross Guest Suite on Historic Homestead

Florence

Martha F.

A large, two-story house with a wrap-around porch, a brick chimney, and a small garden area with a bench.

8. The Dewey

Lenox

Thea

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

9. Sturbridge Country Inn

Fiskdale

Christine

CA $390 total

includes taxes & fees

Nov 13 - Nov 14

A cozy kitchen with a dining area, large windows with a view of greenery, and a built-in bench with cushions.

10. Renovated Private Guest House by Evergreen Home

Great Barrington

Rob and Cindy H.

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

11. Cheney Bros Hill Top Mansion

Manchester

Marc

A sign for The Retreat at Norwich Lake, a Timothy Hill Retreat Center, surrounded by trees and a gravel path leading to a building with a wooden facade.

12. The Retreat at Norwich Lake

Huntington

michael

A two-story house with a stone pathway leading to the front door, surrounded by a well-maintained garden and trees.

13. Cliffwood Cottage by Evergreen Home

Lenox

A white house with a porch and an American flag.

14. 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