Pittsfield Vacation Homes

A historic building with a prominent tower and an American flag.

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Our top choices for Pittsfield holiday homes

A covered outdoor seating area with wooden benches and a view of a fenced property.

1. Peaceful Country Escape - High Speed Wifi

Pittsfield

HK$1,846 total

includes taxes & fees

20 Nov - 21 Nov

A two-story house with a wooden deck and a garden with colorful flowers.

2. COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Bluffs

Brian G.

HK$1,622 total

includes taxes & fees

6 Nov - 7 Nov

A spacious room with hardwood flooring, a grand piano, a comfortable armchair, and a chandelier.

3. The Yellow Rose Historic Home

Louisiana

Brendan R.

HK$2,737 total

includes taxes & fees

3 Nov - 4 Nov

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Top Pittsfield Hotel Reviews

William Watson Hotel

10/10 Excellent

"Great place"

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

10/10 Excellent

"This is an expensive property and home, very well maintained, easily able to accommodate a large family group. The large inground pool with slide and a diving platform was fantastic. The young children in our group spent the majority of their time in the pool! The adults enjoyed the pool just as much. Just as great was the tennis court with Pickleball area and basketball court. Our group also made good use of the game room with billiards, ping-pong, foosball. This is a very fine oasis with something for everyone to do!"

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