Pittsfield Vacation Homes

A historic building with classical architecture, a traffic light, and a yellow taxi.

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Our top choices for Pittsfield holiday homes

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Liz V.

HK$4,319 total

includes taxes & fees

26 Jul - 27 Jul

Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

HK$9,540 total

includes taxes & fees

27 Jul - 28 Jul

White Lily Lodge 50 acre estate with private lake

Cropseyville

HK$7,163 total

includes taxes & fees

29 Jul - 30 Jul

Coffee/tea maker, fridge, microwave, stovetop

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Nancy H.

HK$4,447 total

includes taxes & fees

20 Aug - 21 Aug

Comfortable Berkshires retreat on mtn resort, SISO

Hancock

"The location was excellent, within walking distance of ski trail. Wonderful view of the ski area and surrounding mountains. The fireplace was perfect for the end of the day. Our large family had plenty of space to have fun together or chill alone. We had concerns about the cleanliness and working conditions of some electronics. Our concerns were communicated with the owner, and the response was positive. I am sure with corrections this Comfortable Berkshire Retreat will be a 5 star stay. "

Russell R.

HK$4,758 total

includes taxes & fees

28 Jul - 29 Jul

stylish Berkshires Retreat

Lee

Donna K.

HK$3,259 total

includes taxes & fees

3 Aug - 4 Aug

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

HK$2,752 total

includes taxes & fees

30 Jul - 31 Jul

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Top Pittsfield Hotel Reviews

Berkshires Untold

10/10 Excellent

"Really nice breakfast and good decir"

Vacation Village in the Berkshires

10/10 Excellent

"The king deluxe suite was large enough for a family. The kitchen was sufficiently equipped to cook meals. The in room jacuzzi was comfortable for two. The outdoor pool was large and there were plenty of lounge chairs for the guests. The indoor pool was large as well, though a bit noisy. The views were very nice and the location is relatively close to Williams town, Pittsfield and Lenox. Lots of museums and other sights in the area. Overall a very nice location for long weekend or a full week."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"I liked the gym, bed, pillows, TV stations selections. I didn't like the location of the room safe which was literally floor level and practically impossible to access. The couch in our room seemed to be missing a cushion to allow one to rest against."

FairBridge Inn Express

8/10 Good

"Room was clean and in excellent condition - apparently they have totally renovated since earlier reviews that mentioned severe problems. The exterior could use some paint, but the room was perfectly clean and fairly spacious. All the little things, like good A/C, shower temp/pressure, a working mini-fridge, etc., were completely fine. Complaints: I couldn't get the WiFi to work. Also: it's not in the most scenic part of Pittsfield, but it's just minutes from the nicer areas, and a short walk to fast food or decent chain restaurants like Friendlys, Applebees, and Starbucks."

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