House holiday rentals in Stockbridge

We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

We had a great stay at William’s. The location was beautiful and the house was comfortable. We had a great mix of day-tripping and relaxing with a view. We also ran into William and he was very helpful and friendly.

We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

Great location and lots of space. We were able to ski in/out (look for "Cliff's Road" sign when skiing back) fairly easily, which was nice. Would definitely stay here again. Thanks!

Very quiet and cozy. Comfortable beds. Lots of room for everyone.

Great spot for a week of skiing! Danielle was very helpful and communicative throughout

Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

Andreas place was gorgeous and looked just like the pictures. The house was clean and organized and the backyard was wonderful to relax in.

Perfect place for a Killington/Pico/Okemo ski getaway. Everything was easy to find with clear instructions. Hosts were responsive. My kids (ages 17 & 13) loved the loft. High quality white noise machines were great. We’d stay here again anytime.

We checked in to Kalyn’s house just before a storm gave us 15” of fresh snow. What a great place to get cozy in the winter! The house is remarkably clean given its rustic charm. The beds and bedding were all amazing. The record collection and fireplace set the mood for cooking and enjoying a meal. Our two sons and sheepdog Denver loved it too!

Perfect location for us and what we can to Pittsfield for. We had plenty of room for five of us. Nice to have a bedroom for everyone. Kitchen was equipped to do anything we wanted to as far as cooking etc Close to skiing Loved being on 60 acres. All worked out perfect for all of us

Great spot, it was perfect for what we needed! I love how secluded the house feels, I wish we had better weather so we could have enjoyed the outdoor firepit and the front porch more. The house had everything we needed and everything was clean and comfortable!

Martina was a perfect host. The rental worked well for six adults and two infants.

The perfect place to stay on a ski vacation! 15 minutes from Killington with a hot tub in picturesque scenery to unwind after the day while looking at the stars.

We had a great stay, house was very accommodating and beautiful. Plenty of space for our family of 7 (2 adults, 5 children ranging in age from 17-10months) Beautiful surroundings, quiet and peaceful our entire stay

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!

David was very friendly and responsive. We enjoyed the location and the peaceful atmosphere. I was with my sister. The stay was a great experience and felt well worth it. Just a note—one bedroom is accessed via a spiral staircase, another by a ladder, and there’s a sleeper couch in the living room. Would definitely recommend!

Had an absolutely great stay! Cant say enough great things about it. The house was super clean, was cozy and felt right at home. The home was placed in the perfect location, only 10 minutes from Killington and was very private. It had a nice outdoor area, with a nice creek, an outdoor patio and large outdoor space.

Impeccable vibes, Britt's home is absolutely darling with plenty of comfortable and clean space and a laid-back feel. Close drive to skiing and town. Home is stocked with all you need and plenty more. Great communication with the host. Would gladly return next year.

Fabulous place! Really a fun and one of a kind place to stay! Everything you need is right there making it an ideal place for overnights or travel but with more character and privacy than a hotel. Just be warned the bed is extremely comfortable and may require a xtra motivation to get out of in the morning :)

We really enjoyed our five nights at the Hop House. The place is exactly how it is described/pictured. It isn’t super fancy, but it has a cozy charm that made us immediately feel at home. The back deck is built around a couple of trees! It feels like a treehouse, and from there you can enjoy views of the horses in the pastures and a few cows across the street! The kitchen was well stocked and Dorothy left us coffee and a little bottle of maple syrup! We enjoyed our visit and would definitely stay again!

Stayed at Ashley’s place for a family hiking trip in May- the location was peaceful, the house was cozy, complete with fireplace and nice decor. Was the perfect complement to our outdoorsy weekend!

This was my second stay at this lovely home. It is very convenient to Routes 100 and 125. I love the babbling brook behind the house. It's always clean and has everything you need!

Had another great stay at this Airbnb. This was our second time, and we look forward to visiting again. It’s a great property at a reasonable price.