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

Guest Houses in Hampshire County

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Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27

Our top choices for Hampshire 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

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (430 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is NT$3,226
NT$3,603 total
includes taxes & fees
Oct 29 - Oct 30
The Central Downtown Inn & Suites
A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

2. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (66 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."
United States
Barbara
The price is NT$3,650
NT$4,077 total
includes taxes & fees
Nov 2 - Nov 3
Hideaway Inn Lenox
A two-story house with a porch, a balcony, and a chimney.

3. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (151 reviews)
"Like the ambiance as well as the decor! The location was perfect for walking around town!"
United States
Robert
The price is NT$2,317
NT$4,185 total
includes taxes & fees
Nov 4 - Nov 5
Blooming Inn
A living room with a fireplace, two sofas, and four black side tables.

4. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (42 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
The price is NT$4,891
NT$5,463 total
includes taxes & fees
Nov 11 - Nov 12
The Revival House
A stainless steel refrigerator with a digital display showing the time and date, a microwave above it, and a kettle on the stove.

5. 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)
"So clean and comfy"
United States
Anonymous traveler
The price is NT$11,405
NT$17,176 total
includes taxes & fees
Nov 10 - Nov 11
Upscaled Home in a Quiet Neighborhood
A spacious room with a large wooden floor, a patterned rug, a sofa, and a dining table with chairs.

6. The Dewey

The Dewey
3.5 star property
Lenox
8.6 out of 10, Excellent, (330 reviews)
"We would definitely stay here again! "
United States
Thea
The Dewey
A white two-story building with a central entrance, columns, and an American flag.

7. Sturbridge Country Inn

Sturbridge Country Inn
2.5 star property
Fiskdale
4.8 out of 10, (118 reviews)
"Room was very clean and loved the rustic country decor. Fire place and jetted tub worked perfectly. "
United States
Christine
The price is NT$8,147
NT$9,100 total
includes taxes & fees
Nov 5 - Nov 6
Sturbridge Country Inn
A room with large windows, wooden beams, and a bed with floral pillows.

8. Chestnut Lodge

Chestnut Lodge
3.5 star property
Lee
2.0 out of 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...
United States
Priya
Chestnut Lodge
A cozy living room with a stone fireplace, leather sofa, and a wooden coffee table with flowers.

9. Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch
3.0 star property
Lee
Jacob's Tanglewood Ranch
A bedroom with a wooden bed, a nightstand, a dresser, a rug, and a window with curtains.

10. YLD Rooms Rome - Shared Bath & Spaces

YLD Rooms Rome - Shared Bath & Spaces
2.0 star property
Forest Park
YLD Rooms Rome - Shared Bath & Spaces
Fitness facility

11. Angels Rest Retreat

Angels Rest Retreat
3.0 star property
Leyden
10.0 out of 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. "
United States
Sharon
Angels Rest Retreat
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 Hampshire County Hotel Reviews

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

10/10 Excellent
"Cannot say enough about how great this property was. I was able to get a ride from the airport and back to the airport. Rooms were super clean. It was nice to have a breakfast. Staff was really friendly shower pressure was great. There was an idin jn the room, everything that you could possibly want in a good hotel stay was there at an incredible price."
geoffrey 2-night trip
Posted 6 hours ago
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Find out more about Hampshire County

Hampshire County Guest Houses information

Number of reviews
1,032
Accommodation
11 Guest Houses
Lowest Price
NT$3,603
Highest Price
NT$17,176

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