Pittsfield Guest Houses | Find the Top Guest Houses in Pittsfield

A lake surrounded by autumn-colored trees and a rocky shoreline.

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Our top choices for Pittsfield guest houses

A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.

1. The Trailside Inn

North Sherburne

Marc

includes taxes & fees

26 Oct - 27 Oct

2. Killington Haus

Killington

Ivan

includes taxes & fees

20 Oct - 21 Oct

A spacious room with a large bed, a sofa, and a chair, featuring large windows and a view of greenery outside.

3. Lincoln Inn & Gallery

Woodstock

Ingrid

includes taxes & fees

22 Oct - 23 Oct

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Top Pittsfield Hotel Reviews

Emrose Luxury Cabins

8/10 Good

"Would stay again"

The Mountain Inn at Killington

10/10 Excellent

"Our family enjoyed our one night stay at The Mountain Inn, including our 7 year old kid and our dog. It was nice to find a hotel that was very welcoming to dogs and only charged $35 per night for him, staff were friendly, and we loved swimming outside in the 95 degree heated pool while the temp outside was near freezing, it was amazing. The room was clean and recently renovated, and the grounds and restaurant were on par with what we expected. The restaurant had live music Saturday night and the old fashioned I had with their house made bourbon from their distillery was delicious, while the burger, salad, and Bavarian pretzels were pretty good, and the cheese pizza was not so good but the kid liked it. We enjoyed the view of the nearby mountains, foliage, and short drive over to Thundering Brook Falls. The continental breakfast was included and could have been better, and had we stayed a few more days we would have explored more of the food and shops in the area, as it seems like there were a few. We could probably suggest some upgrades to the game room but we had fun in there regardless. Overall, we liked our stay at The Mountain Inn and found that it met our expectations for the value, and the welcoming staff, heated pool, and accommodations could have my family going back in the future."