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Compare 343 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (141)
"Great place and views. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
Peace and quiet on the lake
9.6 out of 10, Exceptional, (190)
"Loved it!"
Peace and quiet on the lake
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (19)
"The house is lovely and so perfectly located. The two bedrooms were sufficiently apart and next to their own bathrooms so both couples had privacy.the screened in porch was perfect to hang out and play cards at night and my dog absolutely loved the back yard. The location is superb, conviently located central to Stockbridge, ,lenox and Great Barrington. Fifteen minutes to Tanglewood and the Norman Rockwell museums. There are so many hiking trails with fabulous mountain views nearby."
Stockbridge Home, Come Experience The Berkshires!
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (213)
"We had a great stay at the carriage house! The property was incredible, we especially loved the variety of trails to explore. Our hosts were very helpful with directions and local recommendations. The house was charming and cozy. Would visit again! "
Berkshire Village Carriage House - Super Private!!
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (36)
"We had a wonderful stay as a group of 6 adults and 2 children. The house was very comfortable and clean. We appreciated the well stocked kitchen and excellent set up for kids. The location felt private but was still only a few minutes drive from Great Barrington. Thank you for a great visit! "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (10)
"Enjoy easy access to Laurel Lake, Lenox and High Lawn Farm from this lovely space! A quick walk to the dock across the street affords time by the water to read, swim or kayak. The kitchen is nicely appointed, the house heats and cools very efficiently and the owners are wonderfully communicative. Had a great stay and would return!"
Private Access To Laurel Lake, Enjoy Lake Life
Garfield Townhouse in the Berkshires on Main St
10.0 out of 10, Exceptional, (8)
"We very much enjoyed our stay at Garfield House and hope to be back someday. Our host Jeff was responsive and available for anything we needed. The unit was clean and set up just as shown. Highly recommend to anyone interested in staying in a great Berkshire town."
Garfield Townhouse in the Berkshires on Main St
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is SAR 983
SAR 1,997 total
includes taxes & fees
23 Sep - 24 Sep
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
10.0 out of 10, Exceptional, (32)
"Relaxing, quiet, beautiful property. We really enjoyed the views, exploring the grounds and it is a short trip to Stockbridge. We had a wonderful stay. "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
10.0 out of 10, Exceptional, (3)
"Location was perfect for a smallish family gathering 7ppl. Very comfortable and relaxing place. "
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (9)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"I don’t want to publish review, but I really think the owners should let people know that two of thee bedrooms are in the basement and one has no windows. Also a big issue is the firing range next door. Gunshots every day and a poor dead bird on deck. Afraid to go outside!!!"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (122)
"My partner and I were in MA to drop our eldest at Smith College for their first year. We chose Flight's End for the location and the fact that we were allowed to bring our pups with us. It was incredibly peaceful and just what we needed during an otherwise emotional time with such a big transition for our family. "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Berkshire Lake access
10.0 out of 10, Exceptional, (46)
"Our stay was fabulous. The house was beautiful and well maintained and equipped. Joni was easy to work with and always available. "
Berkshire Lake access
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (104)
"House was as described. Lake was really nice. We used the 2 kayaks, pedal boat and floaty — lots of fun. There are lots of reeds and sea plants growing around the dock, so we went swimming off of the pedal boat further into the lake. Hot tub was great. Fire pit too."
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Wellspring by AvantStay | Indoor Pool + Views
10.0 out of 10, Exceptional, (6)
"The location could not be better in terms of being close to West Stockbridge yet also feeling very remote and with beautiful views. The pool was great. We thoroughly enjoyed ourselves."
Wellspring by AvantStay | Indoor Pool + Views
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (15)
"This was a beautiful, spacious, and peaceful place for us in our friends to get together. It was centrally located to everything we wanted to do. Amanda was wonderful in her communications and everything was clean and ready for us."
The price is SAR 525
SAR 1,307 total
includes taxes & fees
24 Sep - 25 Sep
Near Tanglewood: Historic Summer Retreat
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Other property types in Pittsfield

Chic Pittsfield Home With A View!
9.2 out of 10, Wonderful, (5)
"We enjoyed our week in Pittsfield and at this home. The house was as described and expected, and it offered the privacy and seclusion we wanted. At the same time, the house is very conveniently located, and activities, beautiful walking trails, and restaurant options were nearby. We very much appreciated the reliable WiFi as some of our party had to work remotely during the week. Also, our pup loved the fenced in yard, the deck is great, and we enjoyed use of the fire pit. Would return again if...
Chic Pittsfield Home With A View!
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1713)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is SAR 633
SAR 732 total
includes taxes & fees
23 Sep - 24 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (897)
"Was good everything "
The price is SAR 559
SAR 613 total
includes taxes & fees
14 Oct - 15 Oct
Jiminy Peak Mountain Resort
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.