Search Vacation Homes in Pittsfield
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Pittsfield vacation homes
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
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
Liz V.
The price is AED 988
AED 1,814 total
includes taxes & fees
13 Apr - 14 Apr
Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy PeakHancock
10.0 out of 10, Exceptional, (19 reviews)
"Amazing Inn. Cozy and everything we needed. "
Price F.
The price is AED 2,272
AED 4,173 total
includes taxes & fees
13 Apr - 14 Apr
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
Matthew F.
The price is AED 588
AED 1,449 total
includes taxes & fees
13 Apr - 14 Apr
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is AED 536
AED 1,382 total
includes taxes & fees
12 Apr - 13 Apr
Florida Mountain Log Cabin
Florida Mountain Log CabinFlorida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
The price is AED 675
AED 1,245 total
includes taxes & fees
12 Apr - 13 Apr
Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
maureen k.
The price is AED 754
AED 1,178 total
includes taxes & fees
13 Apr - 14 Apr
Cozy Riverside Berkshires Retreat
Cozy Riverside Berkshires RetreatGreat Barrington
9.2 out of 10, Wonderful, (13 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
Cristine C.
The price is AED 744
AED 1,163 total
includes taxes & fees
14 Apr - 15 Apr
North Getaway Cottage
North Getaway CottageWilliamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
Carole S.
The price is AED 744
AED 1,643 total
includes taxes & fees
13 Apr - 14 Apr
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Pittsfield Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
