Kid-friendly vacation rentals in Pittsfield

My husband and I had a wonderful stay at Sarah's historic home with our two grown children. The house was clean and extremely comfortable with lots of space for all of us. We felt welcome from the moment we stepped through the door. From the personalized welcome sign, to the flowers and wine and so many extras not usually provided... coffee, mints, tissues, throw blankets, an emergency kit, plenty of towels, and a new toothbrush for my husband who forgot his. The weather didn't cooperate for us to use the outdoor spaces, but we can imagine how wonderful it would be to enjoy the porch and the back deck. We highly recommend staying here if you are in the area.

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!

Wonderful place on the lake with a great host. Janice was very responsive, offered an early check-in and set up a baby gate. Great place for dogs and kids.

John and Angela are incredible hosts and we’re so kind to us. They very clearly care about their guests and we are excited to stay here again. Their home had all the “creature comforts” someone traveling can ask for. Comfy linens, stocked bathrooms, fully stocked kitchen, large living spaces, and a great backyard space. Total gem!

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.

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.

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.

This was my second time staying here and it’s perfect what I needed. I come up from the city to work Saratoga racetrack and just need a place to lay my head. It’s great affordable and clean. If you’re interested in downtown Troy, it’s a quick 10 minute drive. Also there is a Stewart’s close by. John and Shauna were very accommodating on both my visits!

My new go-to place in the berkshires! I love the berkshires for hiking , my favorite spa (mend), and all the cute shops/food outings! This spot was perfect - it's well-decorated, the bathroom is nice, and the location is GREAT! Loved the back patio for morning coffee. Washer/dryer was fast. Host is very responsive and helpful. Looking forward to my next stay & would love to bring my dog next time :)

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

We had a great time at this lovely spot! Erin was a very kind and responsive host, and the apartment was just as described :)

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.

Carla was a wonderful host. More importantly her rental was beautiful and very comfortable. Would strongly recommend and we look forward to going back (when there’s less snow)!

Stunning location a short walk through lovely Congress park to downtown Saratoga. Scrumptious bakery in easy walking distance. The apartment was delightful: very clean with all the essentials stocked. We loved being able to stop back in during the day for a quick recharge before getting back into the middle of everything. Bright and sunny during the day and quiet and peaceful at night.

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.

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