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
31 Jul - 2 Aug
In two weeks
7 Aug - 9 Aug
In one month
21 Aug - 23 Aug
In two months
18 Sep - 20 Sep

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, (26 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 486
AED 543 total
includes taxes & fees
26 Jul - 27 Jul
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, (379 reviews)
"Central location!"
United States
Brenda
The price is AED 393
AED 439 total
includes taxes & fees
26 Jul - 27 Jul
The Central Downtown Inn & Suites
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (36 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
26 Jul - 27 Jul
The Revival House
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (142 reviews)
"Appealing common spaces, lovely selections at the coffee/tea station, library and games. Everything for a cozy respite in a great location. Walk to the local village and attractions, central to exploring the Mohawk Trail."
United States
Annette
The price is AED 398
AED 625 total
includes taxes & fees
17 Aug - 18 Aug
Blooming Inn
Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (288 reviews)
"This place was really great! Better than the photos. Clean and cute and quiet."
United States
Adam J
The price is AED 661
AED 981 total
includes taxes & fees
28 Jul - 29 Jul
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, (111 reviews)
"We loved our stay! The cottage was adorable!"
United States
Kristen S.
The price is AED 496
AED 916 total
includes taxes & fees
29 Jul - 30 Jul
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, (127 reviews)
"Very nice stay"
United States
Peter B.
The price is AED 496
AED 747 total
includes taxes & fees
23 Aug - 24 Aug
In town, newly remodeled studio with private balcony
Lounge

The Dewey

The Dewey
3.5 star property
Lenox
8.6 out of 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."
United States
Casey
The Dewey
Miscellaneous

Sturbridge Country Inn

Sturbridge Country Inn
2.5 star property
Fiskdale
4.8 out of 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"
United States
Russell
The price is AED 863
AED 964 total
includes taxes & fees
27 Jul - 28 Jul
Sturbridge Country Inn
Comfort House, 4 Bedrooms, Non Smoking | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

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 1,157
AED 1,790 total
includes taxes & fees
26 Jul - 27 Jul
Upscaled Home in a Quiet Neighborhood
Property grounds

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!
Coffee/tea maker, fridge, microwave, oven

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

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
Exterior

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
Lenox
Cliffwood Cottage by Evergreen Home
Fireplace

Jacob's Tanglewood Ranch

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

Motel 6 Enfield, CT - Hartford

Motel 6 Enfield, CT - Hartford

8/10 Good
"It was great for the price! The bed was not very comfortable and the bright lights from outside made it seem like daytime. The blinds blocked most of it, but if you're someone that needs it dark, you won't have that in the rooms at the front where lights are shining on the signs. Getting the room cleaned was tough. You have to tell them you want it done. When they didn't do it after the request, they said it was because someone was in the room. Then, they said it was because no one was there and they couldn't clean without us present. This was super awkward."
Colleen 8-night trip
Posted less than an hour ago
Motel 6 Enfield, CT - Hartford

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