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Our top choices for Pittsfield vacation homes

Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy PeakHancock
10.0 out of 10, Exceptional, (21 reviews)
The price is ¥93,414
¥175,424 total
includes taxes & fees
Jul 14 - Jul 15

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!Pittsfield
8.0 out of 10, Very Good, (8 reviews)
The price is ¥56,601
¥97,099 total
includes taxes & fees
Jul 26 - Jul 27

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cozy Escape in a Suite near Bryant Mountain State Forest in MassachusettsCummington
10.0 out of 10, Exceptional, (1 review)
The price is ¥17,663
¥22,095 total
includes taxes & fees
Jul 10 - Jul 11

Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
The price is ¥14,758
¥54,528 total
includes taxes & fees
Jul 16 - Jul 17
The price is ¥18,814
¥33,232 total
includes taxes & fees
Jul 14 - Jul 15

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Walk into town, soak up sun on enclosed porch & steps away from nature trails!Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
The price is ¥105,255
¥177,712 total
includes taxes & fees
Jul 19 - Jul 20

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington, Cabin Sleeps 14, Walk To TownGreat Barrington
9.6 out of 10, Exceptional, (48 reviews)
The price is ¥269,705
¥403,116 total
includes taxes & fees
Aug 2 - Aug 3
The price is ¥42,538
¥71,561 total
includes taxes & fees
Jul 21 - Jul 22
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

Quality Inn Great Barrington
10/10 Excellent
Find out more about Pittsfield
Pittsfield Vacation Homes information
Number of reviews | 14,815 |
|---|---|
Accommodation | 435 Vacation Homes |
Lowest Price | ¥10,800 |
Highest Price | ¥45,107 |

















































































