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Check prices for these dates

Next weekend
16 Jum. I - 18 Jum. I
In two weeks
23 Jum. I - 25 Jum. I
In one month
6 Jum. II - 8 Jum. II
In two months
4 Raj. - 6 Raj.

Compare 7 Guest Houses in Pittsfield with updated reviews, rates, and availability.

The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (278)
"The big plus about the whole stay was "
The price is SAR 388
SAR 434 total
includes taxes & fees
19 May - 20 May
The Central Downtown Inn & Suites
Hudson valley and The Berkshires Cottage
Exterior

Hudson valley and The Berkshires Cottage

10.0 out of 10, Exceptional, (5)
"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 SAR 383
SAR 1,242 total
includes taxes & fees
9 May - 10 May
Hudson valley and The Berkshires Cottage
Renovated Private Guest House by Evergreen Home
Outdoor dining

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
Interior

Guest House Sanctuary by Evergreen Home

Guest House Sanctuary by Evergreen Home
Jacob's Tanglewood Ranch
Dishwasher

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Vanderbilt Lakeside
Exterior

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
Exterior

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
Interior

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

Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is SAR 2,059
SAR 3,890 total
includes taxes & fees
12 May - 13 May
Hancock Village Inn at Jiminy Peak
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

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

9.8 out of 10, Exceptional, (141)
"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
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (56)
"Perfect lake front home to get away for a quick weekend trip with the family over the holidays!! Location, location location, close proximity to downtown Pittsfield, 15 from Jiminy peak & Bousquet Mt. Andrey was extremely helpful throughout the process with suggestions for food and activities for the kids. The house was a perfect fit for our family and friends. Everyone enjoyed their time there and would definitely book again"
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.