Kid-friendly vacation rentals in Stockbridge

Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

Our crew enjoyed their stay in Mary's home. She was very friendly and proactive with directions to her home.

This is our third stay at Kevin’s place. It is a home that has brought wonderful family memories for us over the years. The stunning lakefront views, large porch area and sleeping arrangements are perfect for two small families. The game area is perfect for a few drinks and dock on the lake perfect for fishing!

Loved staying here! Really cool New England home, felt very lived in and cozy :) appreciated the toys and games throughout the home for the kiddos. Also the host, Heather is super responsive and kind. Would love to come back in the future

Pulin's place was clean and spacious with plenty of room between neighbors. Great option in the area!

Excellent place for our group. Definitely would recommend. 10 out of 10

Chris isn't joking that he likes to keep the kitchen well stocked. It was great having everything that a typical kitchen would have at your convenience. The views were gorgeous and were really enjoyable when relaxing in the hot tub. Our three boys loved the kids room and that there were toys to play with. The location made our Vermont stay all that much more enjoyable, thank you for the great memories!

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!

Great space, very conveniently located in town. The host was great, and would definitely stay here again

This was a very spacious and cozy spot! A perfect place for a quiet weekend getaway with proximity to hiking and/or skiing/snowboarding. There were many books, games, and puzzles available to peruse and enjoy as well.

Great spot right next to Okemo! The cabin was better than the photos, felt really homey and clean.

Sam is a friendly, generous, helpful host! He and his family live upstairs in this fun, modern building; the apartment is on the ground floor/daylight basement, but the house sits on a steep hill so the unit has plenty of natural light and does not feel like a basement. The separate entrance is located at the far end of the structure so it feels like a standalone unit with plenty of privacy. The neighborhood rises steeply from downtown Woodstock, up narrow, steep, windy roads. The streets were pretty consistently plowed, but drive slowly and cautiously, especially with snow. Also, like Sam says, don't just enter the address into Google Maps; it will try to take you elsewhere through someone's house and yard (haha!) Instead, follow Sam's directions. We loved the casual, yet carefully curated decor and found the bedroom super cozy with the most comfortable bed and linens. Our favorite was going on a cross-country ski adventure right out the back! Thank you, Sam, for a great stay!

Dick and Dorothy are some of the most lovely, hospitable folks we have ever met and we feel so lucky to have gotten to know them through our extended stays at their apartment for the the last 5 winters. Hancock is a truly special community and the apartment is an excellent choice for anyone looking to visit the area. It is conveniently located, well-stocked, and delightfully quaint. We are already excited to return!

The best option for 4 or less people near Middlebury VT. As a previous Vermonter for 3 years, I love the coziness and all the artifacts inside - all seemed very authentic to a Vermonters lifestyle. The hosts are super nice, very friendly, and proactive in providing instructions. The kitchen is especially well-equipped with everything we needed to cook for 4 people, which stands out from all the Airbnbs I’ve previously stayed. We come to VT quite often and it’s disheartening that this is the first time of us finding out about Docs place… Will definitely comeback!

This is a lovely home in a beautiful setting. It is quite close to Stratton and the hosts were all great communicators with a quick response time. I hope to stay there again sometime!

this condo is the perfect set up for our family! we had 3 adults staying, with a dog and a cat. there were three separate full bathrooms which helped a TON. everyone had their own area to wind down. we stayed for easter and were able to cook in the kitchen. Lyn was super responsive with any questions we had! we’re hoping to stay again next easter with Lyn!!

Great place for our ski weekend! Spacious, clean, super comfortable beds, kitchen had everything needed, even spices! close easy drive to slopes! Great host- it was easy to communicate, we felt really welcome in this beautiful place! Would love to come back again and 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

We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.

We had a great weekend getaway! Close to Sugarbush for skiing, surrounding towns and restaurants! Would highly recommend a stay here.

Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!

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.