Family-friendly holiday rentals in Pittsfield

Fantastic place with amazing views for a family ski vacation to Killington. Easy drive to and from the slopes. The hot tub was amazing after a long day of skiing. The views were second to none from both the house and relaxing from the hot tub. Would definitely stay again!

Everything was absolutely beautiful, peaceful, and perfect! Everything was better than I even imagined! Using the hot tub under the stars while it snowed was the most surreal experience! We would absolutely love to come back someday! Friendly hosts, clean environment, and overall very peaceful🩷 10/10

Great place for a vacation stay with friends or family. Hot tub was a nice bonus in the winter after long days skiing. Plenty of sleeping space, clear instructions for everything you’d need in the place

Bob was wonderful and very helpful and responsive during the whole trip. The house was also great and had more than enough space for all of the members of my group. I would very gladly stay there again in the future!

We really enjoyed our stay. This is a beautiful location and home, and is setup to make you feel at home. The host was also extremely responsive which was greatly appreciated.

Dean was very proactive with communicating about our stay and giving helpful tips on getting to his place. It was in a great location. His place was clean and spacious, with everything we needed. We had a great stay! Thanks Dean!

We had a wonderful stay at Cammie’s house! It was more than enough space for 2 families of 5 to spread out! The kids really enjoyed foosball and ping pong. The adults really enjoyed sitting by the fire. The walk to the ski trail was a little tricky as the path was not well traveled and the snow was deep. The walk home from the trail was much easier. One small suggestion would be to have more mugs and more wine glasses available. Overall, a fantastic long weekend!

Alexandro was very helpful and proactive. We contacted him with a washer issue and he had someone come to fix it right away. Amazing ski on ski off accommodation!

Matthew was a very helpful and attentive host. His house was perfect for our multi-generational family get-away. It was comfortable and well stocked with extras, like toys and books, spices, and toilet paper! Matthew's welcome binder and notes made it really easy to feel at home and at ease with the house. We really loved walking off the deck and snowshoeing through the beautiful property. The very private location was so peaceful and relaxing. It was just what we had hoped for for this family time.

This is a great house to stay in. There's a lot of space, places to sleep, sit and relax, eat, watch tv, play games, work, read, cook. Plenty of hot water.. Very private, although in a neighborhood. Nice back yard area when not covered in snow, looking up at the mountains behind. Sheri is top notch. Easy to reach, super friendly and helpful, easy going. We came at the tail end of a snow storm, but the driveway was cleared enough to get our car in and then Sheri worked with us to make sure everything was cleared before we had to go out the next day. Easy walk into the cute town of Bristol. Handful of nice shops (books, games, art, crafts, gifts, toys) and restaurants: Wokky's--ok Chinese/great staff; Minifactory--out of sight coffee/biscuits/sandwiches/fresh ingredients/lot of gluten free; Cubber's--locals' joint/excellent pizza/sandwiches; Farmhouse Chocolates--superb fresh organic truffles, bars, caramels/chocolatier is wonderful. Easy drive to Mad River Glen, Sugarbush for skiing.

Beautiful home, as described. Nice personal touches with towels and mini shampoo/conditioner. Kitchen is large and has most every appliance you would want. Caretaker does come in twice per day but is friendly and unobtrusive. You do need AWD/4WD to access the house.

The Airbnb is perfectly located next to everything in town. Comfortably slept 6 of us and I could easily see fitting another person. Kitchen was fully stocked and had a perfect little space for the group gathering.

Had a fantastic time. Went backcountry skiing before work and then worked from his place with multiple people doing zoom calls without issues. Perfect place for us

A very nice Airbnb for a night or two for a couple. Although, it had more beds to accommodate more than two, the main living area is quite small. Especially, since we had large ski bags with us and no where to really put them. The larger queen bed is up a ladder. I wasn’t going to haul bags up there and The downstairs bedroom has enough room for the full bed and two tiny end tables. It is the smaller of the two spaces, and our luggage would not fit there, so it sat in the tiny living area. Outside of that, the place was very clean, there were nice snacks left for us which I really appreciated and the host was so lovely. She even made us blueberry muffins. The location is about 15 minutes to Manchester and 35 min to Okemo.

The house more than met our expectations! We skied at Killington and Sugarbush and snowshoed on trails behind the house. The house was very cozy and quiet with a large kitchen and very cozy spots to read and sleep in after a long day of being outside. I highly recommend staying here!

Brigid’s beautiful loft apartment was the perfect place to stay during our recent family gathering in Belmont. It’s spotless, well equipped, and located not far from the center of town and Star Lake. We’d love to stay there again next time we’re in Belmont.

I keep coming back as it is a great place, everything is top notch and the hosts are such good people. Highly recommend it if you want a perfect get away

This place was great! Nothing fancy but a great price and plenty of room for me and my friends. Exactly as photographed and described. Foster is also a very nice man! Super friendly. Would definitely recommend and stay there again!

Extremely nice cabin, very recently renovated. The owner has a keen eye for organization, everything is neatly placed where it should be. Linens are clean, beds were super comfortable. Amazing stay, thank you Cathy

Stunning property! We enjoyed a one night stay just to get away as a family. It was so relaxing being able to unplug and cook a full meal in the fully furnished kitchen (which you don’t always have in a BnB.) The dogs loved walking and running outside! We enjoyed soaking up the heat from the wood stove, and playing tunes on the keyboard. Can’t wait for our next stay!

Dray was great - immediate response to any questions. Finding the place and getting in was easy. Had everything you need - maybe could of used a couple extra towels. Beds were comfortable. Great stay!

Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.

Scott is an outstanding host! His place is conveniently located next to the ski slopes, and he was incredibly responsive to any questions we had. Highly recommended!

Our 2nd stay, doesn’t get better than Gabe’s condo! Wish we could have stayed longer. Thanks!