Kid-friendly holiday 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.

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.

Great location with easy access to surrounding areas where there is always something to do! John was very responsive and we really enjoyed our stay in his home. Very comfortable and clean. Quiet neighborhood close to town. Would highly recommend!

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.

My family and I had a great stay here. The property was well kept and matched the description. And the host was responsive and helpful. Would stay again if we're in the area.

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.

A beautiful apartment located in a lovely neighborhood. Walking distance to town and restaurants. Very clean and comfortable.

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 central location. within 2-3 blocks from the NY State Capitol. very good restaurants within walking distance. Nicely done 1 bedroom. spacious. comfortable. very clean. highly recommended.

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!

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

Definitely a space with great level of thoughts and details makes you feel comfortable and relaxed. Surrounded by the nature, you can immerse yourself in the beautiful mountain view and bird chirps, very peaceful and tranquil. We saw deers walking by, rabbit hiding in bush from raining, and a little chipmunk busy around the house all the time. Thanks Katey for sharing her beautiful home and being a great host, super responsive and provides lots of useful information. We had an amazing time!

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!

We are repeat visitors. Staying here is always a pleasure. The apartment is wonderful. Just as described and perfect for day trips or just staying in. Mary and Lance are friendly and courteous. Hope to be able to stay here again when in the area.