Holiday rentals with a fire pit in Pittsfield

We had a wonderful stay at this beautiful home. The beds were extremely comfortable, the house was clean and the kitchen was well stocked. The hosts were very responsive and kind and went above and beyond to make sure we had a great stay. The kids in our group were happy with the toys that were available for them. We would highly recommend staying here for group gatherings. We had a lovely cozy weekend and are so grateful to the hosts!

Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

We loved staying at Erin’s place. Very private, yet so close to all the nearby towns and parks. The place was so comfortable, clean, great bed and linens, and easy to hang out and relax. For sure would love to come again!

Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.

Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family

Lawrence and Ilze are great hosts! They actually just live next to the house and they own a farm. We took our kid to visit their farms with lots of beautiful chickens and roosters. My son even has a chance to feed the chickens. We will definitely come back!

Well equipped, clean, functional space. Back porch and patio is fantastic for expanding the space and ease of entertainment. Caught some pretty good catfish and carp right off the back stairs/landing. Convenient to many amenities with easy access from rt159 and rt57.

Edina and Glen's house was beautiful, spacious, and pristine. It was the perfect setting for a "girls weekend". The grounds were stunning, and made for a great setting. Very close to town, shopping, and wonderful restaurants. We really appreciated that our hosts were very proactive in reaching out and making all instructions clear. They were communicative and flexible. Thank you for having us in your beautiful home! Very memorable weekend.

stayed here the night before my wedding and carrie was such a great host! she was so accommodating and the space was beautiful. there were so many little touches that made our stay amazing! would stay here again!

Very nice place would stay again joy was very friendly had no problems with the place at all tyvm again joy

Our hosts were terrific. The apartment is spacious and bright and well-stocked with coffee! Very convenient to MassMoCa, downtown North Adams, and Williamstown. We'll definitely be returning. Thank you!

We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

Had an amazing stay at this home. We were in town for a wedding and this was perfect for our family and dog. Very clean and easy to walk downtown. I would recommend this place to anyone!

Really clean and perfect for what we needed it for! We were there to move out our daughter from Williams College and it worked out perfectly.

Brent's place was everything we were looking for! We were hoping to have a cozy base to explore Mt. Greylock, Mass MOCA, and Williamstown, and this spot couldn't have been better. Plus, the property itself was fantastic -- spacious, incredible views, and a wonderful outdoor kitchenette/sitting area. Brent is also a very responsive, very nice host.

My wife, dog, and I had a wonderful and peaceful stay at Michael's place. The land is beautiful, the place itself is actually even nicer than the pictures, and there is plenty to do in the area. We will definitely be coming back!

5 out of 5 stars. Used this as an opportunity to get away with my pregnant wife, and we were not disappointed. In fact, we wished that we had booked at least another night or two! The pictures for the listing were great, but we felt the cabin looked even better in person. It was clean, homey, and had everything you needed for a usable kitchen. Lasse’s detailed amenities listing and clear directions in the cabin (like how to properly use the hot tub) far exceeded our expectations. I don’t have one negative thing to say. We are already planning to book for next summer!

Ethan and Debora were very communicative and accommodating hosts. The cottage and its views are exactly as stunning as they look. We stayed during a very cold weekend, and they were very proactive about getting the place nicely warmed up for us before our arrival. Terrific spot for a peaceful weekend!

Clean & comfortable stay that was a perfect location for attending a wedding at Wicked Awesome Events: Amongst the Oaks. Would love to return again for a longer stay—the location is beautiful!

Michelle's Hilltop Cabin in Chesterfield, MA, is a wonderful place. Nestled in the Berkshire woods, but close to the road, and not far from civilization, this place has all the best western Massachusetts has to offer. 11 miles (15 minutes) to Snow Farm (Williamsburg) 17 miles (28 minutes) to downtown Northampton 23 miles (36 minutes) to UMass Amherst 31 miles (44 minutes) to Mass MOCA (North Adams) 32 miles (51 minutes) to Tanglewood (Lenox) The Hilltop Cabin is best for 2-3 people, but Michelle has several other rentals at the same address. See if she has openings to suit your party on your dates. You won't be disappointed!

Beautiful, quiet setting, lovely furniture, all the amenities. Clean and comfortable, and a short drive to shops, restaurants, and hiking trails.

This cottage was Magical. Reminds me of a cottage out of a storybook. Incredibly peaceful and quiet tucked in the woods. The cottage itself was so lovely and Lisa thought of everything. Well stocked with kitchen, bathroom supplies. I loved the games and record player with tons of records. The cottage is super clean and Lisa was an incredible host. I needed to contact her and she was very responsive and thoughtful. I would highly recommend and will be back in the fall ✌🏻

My partner and I absolutely loved our stay at this cabin. The views from the home and the surrounding area were amazing and we found ourselves just slowing down a lot on our drive there to take it all in. Our favorite parts were the hot tub which was so relaxing especially with the backdrop of nature behind us and the amazing kitchen where we cooked all of our meals each day. Most things were around 20 minutes out so it was a very stay at home stay so we really appreciated the effort they made at making the home the main attraction. The host was very communicate and helped solve a minor issue we had right away which was a great experience. Our least favorite part was having to leave! Overall we look forward to coming back again in the future to such a cozy home.

We booked our trip day of to take a long weekend out of the city and I could not stress how perfect it was! We have two kids under 7 and the property provided so much space and safety to run around. On the days it rained, we enjoyed the patio area (with a huge tv). The creek in the back lended us hours of entertainment for our kids and finding the “surprise waterfall” to the left was very exciting! Brianna was available to answer any question we had within minutes. Although we could have stayed at the property the entire time, we tried out some places from the suggested list Brianna left. June Farms was great and the Towne Tavern had amazing wings. We’re excited to come back and sit on the patio during winter months! (They have a heater too!) 10/10 experience