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Compare 448 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (241)
The price is AED 551
AED 837 total
includes taxes & fees
7 Apr - 8 Apr

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is AED 2,017
AED 3,801 total
includes taxes & fees
11 Apr - 12 Apr

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (149)

Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)

Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (212)

Lakeside Retreat Just You, The Lake & The View!
Lakeside Retreat Just You, The Lake & The View!
9.8 out of 10, Exceptional, (69)

Secluded Lux Mansion Pool Home with Amazing Views
Secluded Lux Mansion Pool Home with Amazing Views
10.0 out of 10, Exceptional, (1)

Heart of Lenox Walk to Town Cozy Cottage!
Heart of Lenox Walk to Town Cozy Cottage!
10.0 out of 10, Exceptional, (70)
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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Other property types in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (139)

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is AED 2,017
AED 3,801 total
includes taxes & fees
11 Apr - 12 Apr

Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
10.0 out of 10, Exceptional, (56)
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.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

Life House Berkshires
5/5 Excellent
"Quiet, quick, and easy stay. Clean simple rooms "
A verified traveler stayed at Life House Berkshires
Posted 16 hours ago
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