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Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
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31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Browse Select Pittsfield Guest Houses

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

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (321)
"Nice place "
The price is 2.609.802 ₫
2.915.159 ₫ total
includes taxes & fees
31 Oct - 1 Nov
The Central Downtown Inn & Suites
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (325)
"Great spot. Lots of history. "
The price is 5.150.925 ₫
5.753.715 ₫ total
includes taxes & fees
28 Oct - 29 Oct
The Dewey
The Revival House
Romantic Room, 1 King Bed (Room 4) | Desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
8.8 out of 10, Excellent, (17)
"We thoroughly enjoyed our stay at The Revival House! Super comfortable, clean, and the inside has great decor sensibilities. We will be back if we’re ever in the area again!"
The price is 4.437.720 ₫
4.957.039 ₫ total
includes taxes & fees
8 Oct - 9 Oct
The Revival House
Jacob's Tanglewood Ranch
Dishwasher

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Chestnut Lodge
Property grounds

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
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)
"PERFECT getaway! Gracious, classy Hosts...the Inn is decorated amazingly...all of it is simply breathtaking. A lovely experience. A MUST stay!"
Vanderbilt Lakeside
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 Pittsfield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Very nice!"
PATRICIA 2-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

Find out more about Pittsfield

Find out more about Pittsfield

Pittsfield Guest Houses information

Number of reviews
528
Accommodation
6 Guest Houses
Lowest Price
2.915.159 ₫
Highest Price
5.753.715 ₫