Family-friendly vacation rentals in Pittsfield

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.

I booked a last minute escape from the city and Rob’s mountain getaway was exactly what I needed. The home was both welcoming & comforting with enough blankets to keep me & our furry one warm and cozy. The stocked coffee bar & equipped kitchen made the mornings a breeze. Tucked away in the peaceful mountains of Vermont, stargazing takes on a whole new meaning while in the amazing hot-tub Rob has on the property. The weather was too variable for us to utilize the lovely fire pit but that’s what the winter time is for. Still peaceful to sit up in the ski chairs and enjoy the scenery. We even saw a hummingbird! All in all, Rob is an amazing host with a home filled with so much character and charm. The local restaurant recommendations were all a hit! It’s a quick 30-40 minute drive to Burlington We even extended an extra day because we enjoyed our time so much and Rob was quick to reply and enthusiastic in all communications. 10/10 will stay again and highly recommend!

We had a wonderful stay! It's such a beautiful and unusual cabin. It would be great for two couples as there are 2 equally great bedrooms that are quite separate, and a very nice sitting area around the amazing wood stove. (Which we didn't use because it's June and not necessary.) The hot tub was such a treat, and the bedroom with the boat was so cool. (OK, so maybe the bedrooms aren't quite equally great.) The kitchen is outstanding! We sat out on the porch a lot looking over the meadow, and I really liked that we were able to bring our dog. About the notes and instructions: they didn't bother us at all. There's a few non-intuitive features of the cabin, and it was useful to have clear guidance on those things. I want to make clear why I gave 4 stars for "cleanliness". I think they do an excellent job cleaning this cabin! But a rustic cabin like this is impossible to make "5-star clean". If you want or need that level of cleanliness, then "rustic" isn't for you! Go find a nice hotel.

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!

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

The getaway apartment was just as described. Peaceful, private, and with ample space and amenities for a family of three. We enjoyed our weekend!

Home now after a couple days at the cabin. Feeling fully rested and can’t express enough how much we needed this getaway. Ago and Marty go above and beyond to make you feel comfortable and provide you with everything you could need to relax and have a great time. We will be coming back here. Hopefully soon.

the setting was beautiful and quiet. it was easy for both myself and my niece to find it separately. the linens and the amenities in the kitchen were excellent and the reason that I chose it because I knew we would probably be eating most of our meals together at the Airbnb

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 was the perfect place for a peaceful Vermont getaway! The house is unique and a great balance of historical farmhouse and modern comfort. Very clean and easy to use amenities. Would love to stay 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 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!

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!