Top Guest Houses in Hampshire County in 2026

Hampshire County Guest Houses
Massachusetts
United States of America
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Hampshire County Travel Guide Hampshire County Hotels Holiday Rentals in Hampshire County Hampshire County Car Hire Hampshire County Holidays

A red barn with a metal roof, surrounded by a snow-covered landscape and a wooden fence.

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Our top choices for Hampshire County guest houses

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

A cozy room with a round table, a sofa, a leopard-print armchair, and a large window with a view.

A bedroom with a bed, a fireplace, a staircase, and a TV mounted on the wall.

A sign for 'Hide Away Inn' with 'Hotel Entrance' below it, set against a snowy landscape with bare trees.

1. Hideaway Inn Lenox

Hideaway Inn Lenox

2.0 star property

Lenox

7.8 out of 10, Good, (57 reviews)

7.8/10

Good

(57 reviews)

"Although the property was vintage, the rooms were clean and staff were very helpful and fun to be around. Parking and breakfast were included and the location was excellent."

Barbara

The price is RM569

RM569

RM636 total

includes taxes & fees

13 Sept - 14 Sept

Hideaway Inn Lenox

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

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

A compact living space with a kitchenette, a dining area, and a sofa.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property

Pittsfield

8.4 out of 10, Very good, (410 reviews)

8.4/10

Very good

(410 reviews)

"Large, clean, comfortable suite."

Rena

The price is RM402

RM402

RM450 total

includes taxes & fees

13 Sept - 14 Sept

The Central Downtown Inn & Suites

A living room with a fireplace, two sofas, and four black side tables.

A dining area with a wooden table, four chairs, and a framed picture on the wall.

A bedroom with a bed, a sofa, a fireplace, and a chandelier.

A two-story building with a symmetrical facade, large columns, and a central entrance.

3. The Revival House

The Revival House

3.0 star property

Adams

9.0 out of 10, Wonderful, (37 reviews)

9.0/10

Wonderful

(37 reviews)

"Great place. Large rooms amazing common areas super fun w friends. "

James

The price is RM673

RM673

RM752 total

includes taxes & fees

7 Oct - 8 Oct

The Revival House

A two-story house with a porch, a balcony, and a chimney.

A dining room with a wooden table, chairs, a chandelier, and a fireplace.

A traditional living room with a green sofa, a yellow armchair, a wooden coffee table, and a patterned rug.

A traditional dining room with a wooden table, chairs, and a chandelier.

4. Blooming Inn

Blooming Inn

3.0 star property

Shelburne Falls

9.2 out of 10, Wonderful, (149 reviews)

9.2/10

Wonderful

(149 reviews)

"Lovely Victorian house on a quiet street. Only a few blocks from the center of the town of Shelburne Falls, which is a charming New England town with a lovely river and a beautiful "bridge of flowers.""

steven

The price is RM439

RM439

RM690 total

includes taxes & fees

16 Sept - 17 Sept

Blooming Inn

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

A covered porch with a wooden floor, white columns, and a seating area with chairs and a table.

A spacious library with wooden furniture, large windows, and bookshelves.

A dining room with a wooden table and chairs, large windows with white frames, and a patterned wallpaper.

5. The Dewey

The Dewey

3.5 star property

Lenox

8.6 out of 10, Excellent, (330 reviews)

8.6/10

Excellent

(330 reviews)

"There is no staff on site. Fire alarm went off no one showed up for 20 mins. The shower situation was less than desirable. The property outside was not weeded and lacked any care. Any guest that I spoke to all felt the same. We go once a year to Lenox and will not be staying there."

Casey

The Dewey

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

A rustic room with exposed wooden beams, a fireplace, a bookshelf, and a chandelier.

A room with a fireplace, a large window, and a jacuzzi tub.

A bedroom with a large bed, a bedside lamp, a mirror, and a window with curtains.

6. Sturbridge Country Inn

Sturbridge Country Inn

2.5 star property

Fiskdale

4.8 out of 10, (116 reviews)

4.8/10

(116 reviews)

"the staff was very welcoming took us to our room explained how the fire place and hot tub worked a very enjoyable relaxing stay"

Russell

The price is RM1,016

RM1,016

RM1,135 total

includes taxes & fees

13 Sept - 14 Sept

Sturbridge Country Inn

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

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

A living room with a TV, fireplace, white sofas, and a red rug.

A bedroom with a bed, nightstands, and a wooden floor.

7. Upscaled Home in a Quiet Neighborhood

Upscaled Home in a Quiet Neighborhood

3.0 star property

Forest Park

8.4 out of 10, Very good, (5 reviews)

8.4/10

Very good

(5 reviews)

"So clean and comfy"

Anonymous traveller

The price is RM1,280

RM1,280

RM1,981 total

includes taxes & fees

12 Oct - 13 Oct

Upscaled Home in a Quiet Neighborhood

A cozy living room with a stone fireplace, leather sofa, and a wooden coffee table with flowers.

A wooden deck with a table and chairs, a red umbrella, and a view of a grassy area and trees.

A spacious kitchen with a large island, wooden cabinets, and a chandelier.

A two-story house with a red door, surrounded by a well-maintained lawn and stone wall.

8. Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3.0 star property

Lee

Jacob's Tanglewood Ranch

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

A wooden interior with a patterned rug, a table with a vase of flowers, and a ceiling with antler decorations.

A white house with a porch and an American flag.

A white house with a stone foundation, a green door, and a patio with a table and chairs.

9. Chestnut Lodge

Chestnut Lodge

3.5 star property

Lee

2.0 out of 10, (2 reviews)

2.0/10

(2 reviews)

"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

Chestnut Lodge

10. Angels Rest Retreat

Angels Rest Retreat

3.0 star property

Leyden

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"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. "

Sharon

Angels Rest Retreat

A bedroom with a wooden bed, a nightstand, a dresser, a rug, and a window with curtains.

A room with a wooden dresser, a white door, and a framed picture on the wall.

A wooden staircase with a handrail leading to a landing with three windows.

A room with a floral-patterned sofa, wooden flooring, and a rug.

11. YLD Rooms Rome - Shared Bath & Spaces

YLD Rooms Rome - Shared Bath & Spaces

2.0 star property

Forest Park

YLD Rooms Rome - Shared Bath & Spaces

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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