A historic building with classical architecture, a traffic light, and a yellow taxi.

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Check prices for these dates

Tonight
Sep 14 - Sep 15
Tomorrow
Sep 15 - Sep 16
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Pittsfield Preferred

1. The Orchards Hotel

The Orchards Hotel
Williamstown
United States
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The Orchards Hotel
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Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Spacious, clean, and quiet. It was a little tricky to find the right building, but worth it."
Lynn 1-night trip
Posted less than an hour ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"It was perfect for our weekend away, clean, comfortable bed and a decent breakfast, definitely worth the value:)"
Kimberly 2-night trip
Posted 15 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Loved the pond trail! What a nice shift after a long day on the road."
Deborah 1-night trip
Posted 20 hours ago
The Yankee Inn
Berkshires Untold

Berkshires Untold

8/10 Good
"Location was great! We loved the new addition in the front, where the reception area was, as well as restaurant and bar area, and library. Also liked the fire pits and outdoor seating. Rooms themselves were very basic and motel-like, and rather dark, but they did have nice bath products (shampoo, conditioner and body lotion). We didn’t realize there was also a room darkening shade on the front window, so the first night we just closed the curtain, which was see-thru! Staff was pleasant, and coffee was ready bright and early."
Barbara A 2-night trip
Posted 20 hours ago
Berkshires Untold
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"All the staff I encountered were helpful and friendly. Room was modern and spacious. The free breakfast was very good. I loved the pool and the hot tub! I had an excellent 2-night stay!"
Victoria 2-night trip
Posted 2 days ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Clean room, great location. Perfect base for a weekend in the Berkshires."
Alexandra 2-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"Clean, staff was great, and ample parking"
Michael 3-night trip
Posted 4 days ago
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."
Michael 2-night trip
Posted 5 days ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Big rooms, nice shower pressure. Quiet at night. A great place to stay for enjoying the areas pleasures."
Jennifer 3-night trip
Posted 6 days ago
Hilton Garden Inn Lenox Pittsfield

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