House vacation rentals in Pittsfield

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!

Ashley was super friendly and responsive and her place was as described with everything I need and more to make me feel right at home. Would love to stay here again. Thank you so much for letting us stay at your beautiful place!

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!

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!! 🤩

9 adults and 3 children all met up for a family weekend! We came from NY, NH and Maine! The house was perfect! Plenty of room to gather or separate! Even tho it was a chilly rainy weekend the kids managed to get in plenty of pool time! Tanya was very responsive and Melvin was the greatest! Our first morning he came right over to fix a slow drain. Highly recommend!! Kim and family

We stayed at Skyeburst for a long weekend. The house is even nicer in person with noticeable attention to details like a tea and coffee station and a welcome gift of pancake mix and syrup. The beds were all very comfortable and the house was spotless upon arrival. There is a large mud room which was perfect for removing our gear before stepping into the main house. There are a lot of beautiful design elements throughout the house which makes the space feel inviting and luxurious. Jesse was very responsive and provided clear checkin and check out instructions. We definitely would stay here again.

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.

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!

Six of us stayed four nights in March at Paula’s place. Everything was great. Of the ones that stayed in the bunks all agreed we slept great. Usually bunks are uncomfortable but it was nice here. We aren’t small either. The house had everything we needed and was close enough to the mountain. We had two days of good snowboarding. The access road to the house isn’t great but we all made it fine with a civic, X3, and F150. We would all stay here again. Paula is a great host.

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

The home was exactly what we were looking for. Great accommodations for a large group. Great location

What a wonderful place to get away! This renovated barn was beautiful-clean, spacious, well kept, comfortable and had great views. It is also close to Woodstock, Quechee and all surrounding towns with plenty to do, places to hike, ski, skate. The property managers were highly responsive, helpful and accommodating. We would recommend this place to all!

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.

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!

9 of us spent an excellent weekend here while visiting Rochester for a wedding. Everything was super easy, plenty of room to easily park 4 cars without blocking each other at all. Clear instructions to cover various situations, and added care on Gina's part to give alternative driving approaches to the house in bad weather since the road is a bit steep. We will absolutely be checking the availability of this house first thing whenever we return to Rochester.

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.

Fantastic stay! Absolutely loved this converted gas station. So unique, so much personality. Pictures don’t do it justice. So comfortable and homey. We loved our stay and can’t wait to come back!

We loved our stay at Ed’s place, came with a group of friends to go skiing at Killington for the weekend. We had an issue with the power downstairs and wifi but Ed was very accommodating and responsive. The place matches the photo/description - this place is a gem!

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.