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

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 RM404
RM452 total
includes taxes & fees
1 Nov - 2 Nov
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 RM458
RM511 total
includes taxes & fees
2 Nov - 3 Nov
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 RM290
RM525 total
includes taxes & fees
2 Nov - 3 Nov
Blooming Inn
A hotel room with a tufted sofa, a red floor lamp, a potted plant, a framed picture on the wall, and a bed with a wooden headboard.

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 RM613
RM685 total
includes taxes & fees
16 Nov - 17 Nov
The Revival House
A modern dining area with a glass table, black chairs, and a teal upholstered chair.

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 traveller
The price is RM1,430
RM2,153 total
includes taxes & fees
28 Oct - 29 Oct
Upscaled Home in a Quiet Neighborhood
A large, two-story house with a wrap-around porch, a brick chimney, and a small garden area with a bench.

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 RM1,021
RM1,141 total
includes taxes & fees
29 Oct - 30 Oct
Sturbridge Country Inn
A white house with a porch and an American flag.

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 two-story house with a front porch and a garage, surrounded by lush greenery and trees.

9. Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch
3.0 star property
Lee
Jacob's Tanglewood Ranch
A two-story house with a porch, a chimney, and a brick foundation.

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
Exterior

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
RM452
Highest Price
RM2,153

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