Kid-friendly vacation rentals in West Stockbridge

We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!

Lola's place was clean, quiet, comfy and well situated for our needs. The house is well equipped, including butter, milk and eggs in the refrigerator (nice touch). Lola is very responsive, answering any question we had in a timely manner. We would definitely recommend and stay here again.

Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!

Our hosts were very easy to work with. I felt they cared about our visit and wanted to accommodate us in any way that would make her stay even more pleasurable. The house offered every convenience, including kitchen items for make-at-home meals. Thanks so much, Brandon and Brian!

Great spot to gather with friends. So close to trails and lovely towns. Loved the wood stove and hot tub!

The house was decorated so nicely. It felt like we were on vacation even though we were staying just for the night. Everything was super clean especially the two bathrooms. The host had a lot of amenities like snacks a bottle of wine, coffee tea it was great. We would stay there again

We had a lovely stay! The place was very relaxing, peaceful, and surrounded by nature, yet still close to Woodstock. One of the highlights was seeing a family of deer right outside our window — such a special moment. The hosts were also incredibly accommodating, providing a highchair and pack ’n play for our infant, which made our stay so much easier. We truly appreciated their thoughtfulness and hospitality. Highly recommend to anyone looking for a quiet getaway close to town.

This is the second time time we've stayed at Carol's place. It's spacious, comfortable, with plenty of open rooms. The kitchen is extremely well stocked. This is becoming our yearly must-stay place!

Beautiful, clean home just a few minutes away from the centers of Lenox or Lee in either direction! We had a great time relaxing and enjoying the food nearby :)

Location can’t be beat! This is our second stay in one of Susan’s apartments and the basic needs — linens, dishes, tea etc—are well provided for. She has artful taste which we really appreciated. They also contacted us when we left a shirt behind. They are upfront about the smoke in the stairwell , but the smell does seep into the back bedroom a bit. Also, we were there in April but the building heat was still running. It took us a while to realize that is why it was so stifling hot. We ended up using the AC units to make it comfortable enough to sleep.

This was a great place and Ben was super responsive. I would definitely recommend this spot!

My family and I loved staying at Tj’s place in Hudson. The apartment was beautiful and exactly as described. Four of us stayed there for a week and we were very comfortable. Tj was very responsive when we had questions or issues (which we didn’t have many of since instructions were super clear). I also enjoyed the multiple yoga classes and spa sessions I participated in at their spa downstairs. The instructors and providers were all super friendly! The town of Hudson is incredible for anyone who loves to shop, look at art, and eat good food. It’s small, but there’s so much to see and eat! Everyone in town was genuinely friendly and welcoming. This was exactly what my family and I were hoping for for our vacation. We’re grateful we found Tj’s place!

Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.

My daughter and I had plenty of space to spread out. John’s place is very comfortable, clean, and charming. Thoughtful touches like extra hooks, suitcase stand, and bench at the entry to take off our wet shoes after a rainy Spring day in Hudson. Easy walk to great coffee shop and restaurants. Would definitely return!

The place was as described by the host. Perfect location.

Place is as pictured. Overall was a good stay. Place is clean. The big TV is nice. The kitchen is a nice size. The place is less "polished" than others. Very DIY repairs/renovating but if you're just looking for a place to crash then this is a good spot. The area has some cool food markets and everything is pretty close.

This condo is absolutely beautiful and comfy! We especially love the bed and pillows.

Pristine clean, cozy, one bedroom condo unit located in Windham with seasonal access to tennis courts and a pool. Walking distance to the beautiful Windham Path. Slept better than at home in the comfy bed. Went for two days of midweek remote work. Agnieszka, the host, was gracious and responsive. The host obviously put some genuine TLC into this place and it shows. Browsed for books at Briars & Brambles, an indie bookstore in Windham adjacent to Windham Pharmacy. Purchased groceries and firewood down the road at Hickory Hill Market . Ate in area at Higher Grounds and Windham Diner. Living room has a fireplace with large screen TV just above. Great for all seasons. Thanks Agnieszka!

Luiza was a wonderful host. She provided detailed check in and out instructions, as well as local recommendations for our stay. Her place was exactly as pictured and cleaned wonderfully for our arrival. We hope to be back for another ski trip!

I highly recommend Suzanne's place for anyone visiting Windham! She was incredibly responsive and helpful throughout the booking process and my stay. As someone who travels constantly for work, my schedule can be quite unpredictable, and Suzanne was unbelievably accommodating and flexible with my changing needs. I truly appreciated her understanding and willingness to work with me. The location is fantastic, right in the heart of Windham, and the view of the ski resort from the back deck was an unexpected bonus! I only wish I could have stayed longer. I'm already looking forward to my next visit, not just for winter skiing, but also to explore the beautiful surroundings throughout the year.

Great people great location I would definitely recommend others and a great price

The place was exactly as described and she was really attentive if I had sent a message and it was extremely clean and cozy.

Cozy apartment, walking distance from the water front. Had a great weekend getaway.

We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.