Family-friendly holiday rentals in Pittsfield

The Airbnb was very easy to get to and very nice. It has a very scenic view of the Green Mountains. Also, Mike was a great host and made the stay very easy. It is a great place to stay if you are in the area.

A wonderful ski weekend! We spent two nights and spent the day (Saturday) skiing at Killington. Quiet drive there and back so it was a perfect location to come back to a peaceful evening. Hot tub was amazing after skiing and very clean! Laura and Aaron were very helpful and let us know the conditions of the roads prior to our arrival. Flexible, kind and friendly! Would stay again for sure.

Second time staying and it was better than the first time. Totally recommend and will definitely be going back for our annual ski trip. If it’s available of course!

Great place to stay!

We had a great time at David's place. The kitchen was well stocked, plenty of firewood, and the hot tub was ready to go. The house was very clean. All the bedrooms had plenty of linens, and extra blankets. We would definitely stay at David's again!

Sugarbush Ski House Our stay at this besutiful Airbnb ski house in Sugarbush, Vermont, was nothing short of spectacular. From the moment we arrived, we were impressed by the spacious, modern design and the thoughtful details that made this home a great place for a family trip. The house has nice open floor plan with great views both from in the house and a large deck on the outside. The living room was very comfortable with space for all including two dogs. The kitchen is modern and has great appliances, supplies, and prep area. The bedrooms were large with comfortable beds and modern bathrooms. The other amenities were top-notch. The sauna and hot tub were absolute luxuries after a long day on the slopes, providing the ultimate relaxation experience. Everything was impeccably clean and well-maintained, adding to the overall comfort and ease of our stay. If you’re planning a trip to Sugarbush, this house is not to be missed. Definitely a five star house!!

Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend

Responsive hosts. Directions spot on. Wonderful place. Made a trip to Killington all that much better.

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.

Excellent home in Midd. Would def stay again!

Second time staying here to hike the area trails. The place was immaculate as was my first visit. The hosts are wonderful and helpful. They gave me check in flexibility that added a lot of time to my plans for the day that ended up being a big value. Highly recommend.

We had a great stay, lovely welcoming home and great location - short walking distance to nice places in town and 30min drive to either Sugarbush or Killington/Pico. Thank you!

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.

Rita’s chalet is really clean and the view around it is amazon. The place is well stocked with games for fun and firewoods for warmth. Upon request, Rita was able to accommodate our late checkout request with a reasonable surcharge. We have enjoyed our stay at Rita’s place and would definitely come back next time when we are around

This was a great place for my group! Kitchen had everything we needed, nice TV and fun chatting and games in the beautiful living room. Such a nice little getaway retreat in the woods. Hopefully we’ll be able to come back soon!!

It was a great place for my friends and I to stay.

Chad was an incredible host! He was extremely accommodating with any requests we had. The views from his place are breath-taking! We enjoyed snowshoeing from the backyard onto trails in the woods. I fell in love with his cat who visited daily! He kept the driveway plowed and salted in a timely fashion. We enjoyed our stay and would highly recommend his place!

Amazing stay. Loved how close it was to the mountain. The pool also looked amazing so sad it was winter. Definitely recommend staying there were 4 beds and can comfortably fit 5-6 people.

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

What an amazing place, truly wonderful as somewhere to regain some peace. There are nice walking trails nearby, and the house itself is so welcoming and cozy: an excellent place to play games (there are some available!) or snuggle up with a book in front of the fire. There’s plenty of space, and the kitchen is well-equipped for cooking and baking. And Loraine is a wonderful host: communicative and generous (we made mac & cheese, and she provided us the little flour we needed so we didn’t have to buy a whole bag). The stair steps are narrow, so not a good choice if that is difficult for you, but that wasn’t a problem for us. I’d gladly have stayed much longer!

Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

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.

A wonderful place situated close to the mountain. The amenities were fantastic as well. The only issue was getting the right pin to access the apartment...however Scott responded within seconds so it was minimally disruptive.

Beautiful place, amazing view and location. The view outlooks Pico mountain and all of the trails perfectly. Loved watching people ski from the comfort of the room.