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

Guest Houses in Hampshire County

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
19 Jun - 21 Jun
In two weeks
26 Jun - 28 Jun
In one month
10 Jul - 12 Jul
In two months
7 Aug - 9 Aug

Our top choices for Hampshire County guest houses

BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.8 out of 10, Good, (6 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is AED 545
AED 609 total
includes taxes & fees
24 Jun - 25 Jun
Hideaway Inn Lenox
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (370 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 444
AED 496 total
includes taxes & fees
29 Jun - 30 Jun
The Central Downtown Inn & Suites
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (137 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 388
AED 613 total
includes taxes & fees
30 Jun - 1 Jul
Blooming Inn
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (33 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is AED 608
AED 679 total
includes taxes & fees
16 Jun - 17 Jun
The Revival House
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, (124 reviews)
"Very nice stay"
United States
Peter B.
The price is AED 364
AED 591 total
includes taxes & fees
7 Jul - 8 Jul
In town, newly remodeled studio with private balcony
Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (282 reviews)
"Beautiful “New England” layout and area!!!"
United States
Peter S.
The price is AED 661
AED 985 total
includes taxes & fees
15 Jun - 16 Jun
Berkshire Village Carriage House - Super Private!!
Exterior

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, (107 reviews)
"Cozy spot with lots of thoughtful details. "
United States
Michelle Y.
The price is AED 496
AED 916 total
includes taxes & fees
23 Jun - 24 Jun
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
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 1,053
AED 1,672 total
includes taxes & fees
13 Jun - 14 Jun
Upscaled Home in a Quiet Neighborhood
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
26 Jun - 27 Jun
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, (13 reviews)
"Lovely property, very communicative and helpful host!"
United States
Martha F.
Hill Ross Guest Suite on Historic Homestead
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!
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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hampshire County Hotel Reviews

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

4/10 Poor
"The rooms were old and very musty. The grounds were beautiful, staff was excellent. The prices of the rooms were inconsistent. My daughter and I had the same exact room for the exact weekend and her room was $100 dollars less. Would I recommend this place or stay here again? No"
Maryssa 2-night trip
Posted 1 hour ago
Publick House Historic Inn and Country Motor Lodge