Family-friendly vacation rentals in Pittsfield

Nice place thanks Mike

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!

Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!

My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.

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

We could not have found a better home for our Killington ski week. The ski in ski out directions were perfect and so easy. The home comfortably accommodated 8 adults and provided privacy for each of us as well. Fabulous dining area for our family that provided many happy memories. We've never rented a home where every single bed was so luxurious either. Each night we slept so soundly. On days we did not ski there was plenty to do at the house, a beautiful neighborhood to walk in and such close proximity to Killington Rd with so many dining options.

This is an ideal spot for a winter getaway, and Matt goes above and beyond to provide guests with the best possible experience. During the day, we enjoyed snowshoeing and sledding on the property. At night, the stars truly amazed us. We also enjoyed the cozy fire in the wood stove…a very nice thing for the cold temps we were having. The house is well stocked and beds are comfortable. We are so grateful for the few days we spent recharging at Skip’s Place.

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.

Ideal for a quick college visit. Walkable to campus and breakfast / dinner options. Dog friendly too - exactly what we needed!

There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.

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

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!

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

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

Our family had a wonderful stay at the condo in Killington. The location could not be beat! A very short 5 minute walk to the lifts and Snowshed lodge. The complex had an amenity building with pool/hot tub that the kids loved and the condo was quite spacious and clean. Ruslana was a great host and very responsive! There is a solid chance we will be back next year!

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.

This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place 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

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.