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Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Guest Houses in Pittsfield

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

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (285)
"Very nice place to stay. Recently upgraded. Great location and convenient parking."
The price is SAR 484
SAR 541 total
includes taxes & fees
29 Jun - 30 Jun
The Central Downtown Inn & Suites
The Revival House
Romantic Room, 1 King Bed (Room 4) | Desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
The price is SAR 631
SAR 704 total
includes taxes & fees
16 Jun - 17 Jun
The Revival House
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (313)
"Gorgeous place with clean room and excellent areas to have breakfast, read, and relax. Friendly staff and easy checking process. Would stay here again!"
The price is SAR 604
SAR 675 total
includes taxes & fees
16 Jun - 17 Jun
The Dewey
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (248)
"One of the best properties i've ever stayed at "
Berkshire Village Carriage House - Super Private!!
Hudson valley and The Berkshires Cottage
Exterior

Hudson valley and The Berkshires Cottage

10.0 out of 10, Exceptional, (7)
"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."
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
Cliffwood Cottage by Evergreen Home
Interior

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
Vanderbilt Lakeside
Standard Room, 1 Queen Bed, Partial Lake View | Egyptian cotton sheets, premium bedding, individually decorated

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
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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