Holiday Homes in Pittsfield

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Featured Holiday Homes in Pittsfield

"We enjoyed our stay at this beautiful country home. "

includes taxes & fees

19 Oct - 20 Oct

includes taxes & fees

25 Oct - 26 Oct

"We are 7 sisters aged 50-76. We had a wonderful stay at the Yellow Rose. This beautiful old home had rooms and beds for all of us. Would definitely stay here again"

includes taxes & fees

27 Oct - 28 Oct

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Top Pittsfield Hotel Reviews

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

10/10 Excellent

"Becky and Dave are excellent hosts. We had the best time. The 3 six year olds brought their bikes and had the best time pretending the front driveway was a race track. If you want to make great memories with your family I would highly recommend this house. "

William Watson Hotel

10/10 Excellent

"The room was clean. All the outlets worked and the shower is nice. There are several nice restaurants in a walkable distance. I'd suggest letting the staff know if you will be arriving past 5pm. Check in and check out was very simple. I did not get to sample the breakfast as I was out before it even started. "