Search Guest Houses in Pittsfield

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Compare 8 Guest Houses in Pittsfield with updated reviews, rates, and availability.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (280)
"The big plus about the whole stay was "
The price is AED 437
AED 488 total
includes taxes & fees
18 May - 19 May
The Central Downtown Inn & Suites

Hudson valley and The Berkshires Cottage

10.0 out of 10, Exceptional, (6)
"A great stay in this well situated getaway. The owners were helpful and communicative, and the house was easy driving distance to Great Barrington, Hillsdale and Lenox. The unit is open and airy and decorated in a very pet friendly way. Would stay again without hesitation."
The price is AED 404
AED 1,250 total
includes taxes & fees
19 May - 20 May
Hudson valley and The Berkshires Cottage

Renovated Private Guest House by Evergreen Home

10.0 out of 10, Exceptional, (9)
"Great stay. Cute spot!"
Renovated Private Guest House by Evergreen Home

Guest House Sanctuary by Evergreen Home

Guest House Sanctuary by Evergreen Home

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch

Vanderbilt Lakeside

3.5 star property
9.4 out of 10, Exceptional, (26)
"We loved our stay at the Vanderbilt Lakeside! The house is so stylish and we had a wonderful dinner at the restaurant. Would definitely stay again!"
Vanderbilt Lakeside

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"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...
Chestnut Lodge

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
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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Other property types in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (142)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
19 May - 20 May
Hancock Village Inn at Jiminy Peak

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (56)
"Beautiful lake house that made our trip to the Berkshires very memorable. Perfect home for family and friends to gather."
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
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.