Family-friendly holiday rentals in Stockbridge

Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!

Nice place thanks Mike

This is our second time renting Clinton's ski lodge place is great super host. Always responsive will be renting again next season.

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!

Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!

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.

Great spot near the mountain. nice community pool and hot tub.

Nice place for the 6 of us and dog for a long ski weekend in March. Condo was as described. The kitchen was very clean, nothing in fridge. New fridge and new oven. The bathrooms were very clean. The beds were comfortable. The upstairs space a bit tight for 4 adults, but we managed fine. Two of the twin beds are in an open loft area, which didn’t bother us as we were all going to bed at the same time and waking early to go skiing. Just mentioning this in case you were looking for a 3rd bedroom that was fully enclosed. The Spa and Cafe/ Wine Bar were a great addition to our ski weekend activities. The host was wonderful and very responsive. We highly recommend this condo.

beautiful property. very private. our dog really enjoyed. the patio had swings with the river view it was gorgeous.

This was are 3rd visit and first visit with our 5 + 7 year old. We loved hiking down to the pond and spending the day there on the cute sandy beach. Cool evenings around the fire pit making s’mores was the perfect ending to the day. The cabin was SO clean and a great fit for our family of 4. Thank you!!!

Beautiful property with amazing views! Laura was very responsive and friendly. The apartment was comfortable and cozy for our weekend stay. We would definitely stay here again!

This place is a gem! The location is fantastic – a beautiful, peaceful home right by the river. If you enjoy fishing, the trout are plentiful - we spent several days catching and releasing. The gardens and ponds were stunning. Philip is a terrific host, and the town of Brandon is lovely and just a short drive away. We had everything we needed, whether we wanted to cook in the modern kitchen or eat out at a nice restaurant. It’s the perfect mix of rustic and comfortable. The neighboring garage rental wasn't an issue at all. 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!

It’s very well maintained and private. Everything was as in the pictures and it was a breeze to take care of.

Dawnside is just as beautiful in person as in the photos. We had a wonderful time and appreciated the views, privacy, and cleanliness of the property. Erich is a great host and the house manual is detailed and useful. We would visit again!

We stayed for a few days during our April break and had a nice relaxing time. The area was quiet and the host had a ton of great recommendations in their guidebook for things to/places to eat, but a lot were closed for the off-season/the days we were there, even in nearby Manchester (that's on us, certainly no fault of the host's just something to consider when timing your stay). The house had a unique vibe that our kids especially were thrilled with – as Star Wars fans, they referred to it as the Sand Crawler House. The stream directly across the street provided a fun and peaceful attraction and the trails in nearby Jamaica State Park were beautiful as well. The home was as described, stocked with board games and puzzles, etc., and the EV charger was a nice bonus for our plug-in hybrid SUV.

Beautiful stay with incredibly kind hosts! Pool was lovely and the alpacas were so much fun to pet. Would love to return

My husband and I stayed here to do a few days of spring skiing at Sugarbush. The location is perfect, a short walk to the slopes when there's snow. Two-minute drive to resort if snow is sparse. Sugarbush is a huge resort and has many options for all skills of skiing. The condo was spotless and had a full kitchen with plenty of pots and pans, etc. It was very comfortable and also had a selection of books and games to choose from. Host was very responsive and gave perfect instructions. Thank you!

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!

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!

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.