Search Guest Houses in Pittsfield

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Featured Guest Houses in Pittsfield

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
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
The Central Downtown Inn & Suites
4.0 star property
8.6 out of 10, Excellent, (228)
"Everything was Great"
The Central Downtown Inn & Suites
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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
Hudson valley and The Berkshires Cottage
The price is NZ$542
per night
29 May - 30 May
Hudson valley and The Berkshires Cottage
Jacob's Tanglewood Ranch
3.0 star property
Jacob's Tanglewood Ranch
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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.

Other property types in Pittsfield

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Peace and quiet on the lake
9.6 out of 10, Exceptional, (182)
"We loved our two night stay in the forest :) The house was super clean, well appointed, quiet and relaxing. We didn't have great weather so didn't get to take advantage of the perfect spot on the lake or any of the kayaks or boats, but the location was a great jumping off point for visiting the various Berkshires towns."
Peace and quiet on the lake
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
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.