Guest Houses in Hampshire County

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Check prices for these dates

Next weekend
22 May - 24 May
In two weeks
29 May - 31 May
In one month
12 Jun - 14 Jun
In two months
10 Jul - 12 Jul

Our top choices for Hampshire County guest houses

Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (365 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
The price is AED 419
AED 468 total
includes taxes & fees
1 Jun - 2 Jun
The Central Downtown Inn & Suites
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is AED 634
AED 708 total
includes taxes & fees
18 May - 19 May
The Revival House
Individually decorated, individually furnished, laptop workspace

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (136 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is AED 405
AED 632 total
includes taxes & fees
2 Jun - 3 Jun
Blooming Inn
Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (277 reviews)
"The property is very nice, well stocked amenities. Cozy and warm and perfect for a long weekend getaway. "
United States
Jonathan H.
The price is AED 496
AED 771 total
includes taxes & fees
22 May - 23 May
Berkshire Village Carriage House - Super Private!!
Fireplace, books

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (105 reviews)
"Everything was lovely! The host was welcoming, the cottage was adorable. Amenities were great (fire was on when we got there, warming blankets on the bed). So cozy! Perfect place to snuggle up during the coldest weekend of the year. We'd definitely stay again. "
United States
Jennifer H.
The price is AED 463
AED 881 total
includes taxes & fees
19 May - 20 May
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Property grounds

In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (123 reviews)
"set up great! very clean great location, WONDERFUL"
United States
laurie p.
The price is AED 415
AED 648 total
includes taxes & fees
28 May - 29 May
In town, newly remodeled studio with private balcony
Lounge

The Dewey

The Dewey
3.5 star property
Lenox
8.6 out of 10, Excellent, (329 reviews)
"excellent stay!! The Dewey is a cozy getaway location!"
United States
Chris
The Dewey
Miscellaneous

Sturbridge Country Inn

Sturbridge Country Inn
2.5 star property
Fiskdale
4.8 out of 10, (116 reviews)
"Room was very clean and loved the rustic country decor. Fire place and jetted tub worked perfectly. "
United States
Christine
The price is AED 845
AED 944 total
includes taxes & fees
21 May - 22 May
Sturbridge Country Inn
Fridge, microwave, oven, stovetop

Hill Ross Guest Suite on Historic Homestead

Hill Ross Guest Suite on Historic Homestead
Florence
10.0 out of 10, Exceptional, (12 reviews)
"Lovely property, very communicative and helpful host!"
United States
Martha F.
Hill Ross Guest Suite on Historic Homestead
Comfort House, 4 Bedrooms, Non Smoking | Private kitchen | Full-size fridge, microwave, oven, stovetop

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 AED 1,041
AED 1,659 total
includes taxes & fees
18 May - 19 May
Upscaled Home in a Quiet Neighborhood
Interior

Renovated Private Guest House by Evergreen Home

Renovated Private Guest House by Evergreen Home
Great Barrington
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Cute spot!"
United States
Rob and Cindy H.
Renovated Private Guest House by Evergreen Home
Interior

The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
Granby
10.0 out of 10, Exceptional, (92 reviews)
"Amazing and beautiful place!"
United States
Dillon
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
Front of property

The Retreat at Norwich Lake

The Retreat at Norwich Lake
3.0 star property
Huntington
9.8 out of 10, Exceptional, (17 reviews)
"A truly exceptional pleasure in the middle of nowhere. Peaceful and comfortable. Good for quiet reflection, long walks, or sitting around with family or friends. No amenities and the local area means a 15 to 20 minute drive, but hey, you stay here for the peacefulness of the lodge and sounds."
United States
michael
The Retreat at Norwich Lake
Fireplace

Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch
3.0 star property
Lee
Jacob's Tanglewood Ranch
Exterior

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
Lenox
Cliffwood Cottage by Evergreen Home
Interior

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
Fitness facility

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
Property grounds

Orchard Guest House: Cozy Berkshire Retreat in the Woods

Orchard Guest House: Cozy Berkshire Retreat in the Woods
Rowe
Orchard Guest House: Cozy Berkshire Retreat in the Woods
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

4/10 Poor
"The place is a dump! The breakfast is a bag of crap. There is no coffee. It really harms the Days Inn brand. I will try to avoid Days Inn for future trips."
BILL 1-night trip
Posted 9 hours ago
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport