Kid-friendly holiday rentals in Pittsfield

Our friend group really enjoyed staying here on a rainy weekend in May. Hanging out by the wood burning stove and doing puzzles at the table was a highlight, and our dog loved being able to be outside on the dog run. The location was fantastic - right in between Lenox and North Adams - so we were able to access museums and hikes easily. Would highly recommend!

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!

Beautiful home and a great location!

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.

Excellent stay at this beautiful house! The views were spectacular and everything was as described in the listing.

Cute house, and we enjoyed our stay!

We highly recommend a stay with these seasoned hosts who know how to make a home away from home. This spacious, private location was perfect for our girls' weekend away. The house was clean and comfortable with loads of quirky mid-century modern touches making each room a visual delight. A handwritten note and bag of delicious shortbread cookies welcomed us when we arrived. We loved having the room to spread out and visit and then retreat to our own rooms for rest and relaxation. We did not use the kitchen to make meals, but it was well stocked with a big fridge and plenty of counterspace. The host was responsive and friendly. We hope to make a return trip in the future.

Sylvia’s house is absolutely beautiful! The house itself is amazing, lots of windows and natural light, fairly secluded and private but not remote, it felt safe and serene. Sylvia is a great host, always in touch, and the house was ready for our arrival. It’s probably one of the best homes we stayed at in terms of how well organized it was, the kitchen and the bathrooms had absolutely everything you might think of and even more. We’d absolutely recommend Sylvia’s place to anyone and will happily come back ourselves. Thank you Sylvia!

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!

Mike and Wendy's space was exactly what we were looking for. it was comfortable with all the amenities of a personal home, it was very clean and welcoming. The fridge was stocked with drinks and condiments and the bathroom had extra toiletries! Great restaurants close by.

Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.

Great location, walkable to many restaurants, clear check in instructions

Our stay couldn’t have been better. The listing matched reality perfectly—stairs and all—and the hosts stayed a step ahead with friendly, detailed messages and a useful house guide. The location is superb: an easy stroll to everything in North Adams and a great jumping-off point for exploring the Berkshires. The home itself was spotless, cozy, and wonderfully quiet. The hosts were extremely understanding of a minor issue (our fault) that occurred. We thoroughly enjoyed our visit and would gladly return.

The studio apartment was just what I needed. The kitchen was outfitted with appliances, cookware, and dishes. The bed was comfy. John and Shauna were extremely responsive. A great spot for able bodied folks who need a nice little spot to lay their head while in town.

Wonderful stay! Beautiful home and so much to do in the area. We had a great time!

Wonderful place to stay for an anniversary clean rustic apartment with a welcoming feeling, it felt like a cabin 10/10 would recommend 🙂‍↕️

Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.

We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Such a unique stay! David gave very helpful instructions for arriving and getting to the property, even supplied photos for extra assistance. The property itself is cozy and in a great part of the city. There’s lots to do nearby, super walkable, and David provides great local recommendations. The shared gallery space was so cool to see too. Great experience!

Cozy apartment, walking distance from the water front. Had a great weekend getaway.

My husband and I loved our stay at Jo Anne’s place, it was quite,clean private, easy access to parking and very affordable . Stocked with the necessities.

Great little studio spot to use as your Basecamp for activities in the area!