House holiday rentals in Pittsfield

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!

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.

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.

We had a fantastic stay at this beautiful home. We came with our 6 month old and 3 year old daughters and pup. There was plenty of space for the whole family and very kid friendly. We were saying when we were there that it would have been amazing with a group of friends for a girls weekend too! Beautiful spot where you feel like you’re deep in the Vermont woods but super close to downtown Woodstock. Would love to stay again if available!

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.

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!

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

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.

This place is beautiful! Nothing tops getting to sit out on the balcony and see all the mountains and trees! Just an absolutely amazing view. The house is very well kept and feels both cozy and spacious. The kitchen is stocked with all the utensils and appliances you’ll need and it’s large enough for everyone to stand around in while someone cooks. The couches in the living room are so comfy and great to relax on. There’s a general store about a mile and a half away that’s a really nice walk if you don’t mind going downhill and uphill. Overall, just a lovely space for hanging out and we all really enjoyed everything it had to offer!

Loved this place! It was perfect for a long weekend of skiing and relaxing with friends. Would definitely book again!

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 :)

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!

This was an amazing stay! The house was spotless, and the beds were incredibly comfortable. My family and I felt right at home and enjoyed every moment. The host was always quick to respond and went above and beyond to ensure we had everything we needed. Highly recommend!!!

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.