Family-friendly holiday rentals in West Stockbridge

Hava's place was in a great location, less than a 10 minute drive from town. The town was super cute and had many great places to eat at. We also found the home to be super clean with clear instuctuons and recommendations for anything we needed. Hava was easy to reach and always happy to help us! Would gladly stay here for a small getaway again!

Boris and Rungcheewan’s place was very peaceful and nice. The cabin is private, and has everything you need. They were both proactive in plowing the driveway multiple times throughout our stay to make sure we were safe and could easily access everything. I would highly recommend both this place and the hosts.

My family has stayed here every winter for the last three years and love it every time. The place is awesome for a large family or group, we just hunker in, enjoy the hot tub and fire place. The hosts are helpful and responsive. There is also great places to go close by in Hudson for shopping, some little kid activities and great food. Look forward to our weekend here every year. House has everything you need for kitchen, toys for kids, etc. Don't need to bring a lot!

What a peaceful wonderful time we had in this cherry red cabin. Thank you for warm healing waters, sunny blue skies with mountain views, cozy sleeps and wonderful times cooking and gathering around the cozy cabin. We unplugged, biked the reservoir, ate lots of yummy veggie food, danced at the Bearsville Theater, and breathed in the magical mountain air. Thanks Woodstock and much gratitude to our host Mirav for creating a wonderful retreat. Blessings.

We had an amazing stay! The setting was absolutely beautiful, with stunning views and a peaceful atmosphere. The space was impeccably clean, which made our stay even more enjoyable. One of the highlights was the hot tub – it was the perfect way to unwind after a day of exploring. The host was incredibly responsive and saved us with a last-minute booking, which we are so grateful for. We couldn’t have asked for a better experience. Highly recommend!

House was spotlessly and thoughtfully decorated. The bed was comfortable and hot tub was absolutely phenomenal. Skylights let in beautiful natural light for reading and relaxing. Michael and Enrique were proactive about reaching out beforehand with the house information and we really, really enjoyed our stay. We're not used to baseboard heating so some of the noise from the heating surprised us, but that's to be expected with any place that's not your home. Would gladly stay here again.

We were not able to complete our stay due to a snow storm and loss of power and a family member with a medical condition that didn’t allow us to “wait & see” on the return of power so we were only on the property for about 20 hours. However with that being said the host was extremely kind and provided us a full refund which she didn’t have to do. The directions were excellent and the pre- rental information accurate and helpful. This is the place to go if you want to disconnect cell phone service is pretty non existent unless you have Verizon. The views are amazing from almost every room. Beds are comfortable and house furniture exactly what you would expect in a cabin. I posted on my social media about my holiday that fell apart and received questions about the home and have already recommended it to 3 families.

Amazing cabin , close to everything, clean ,

The loft was lovely: fireplace, large balcony, view down the mountain, TV with airplay support, kitchen, etc. the surrounding was quiet and peaceful. The host was responsive and very friendly. Would recommend to others.

Small and quaint place to stay as a home base for hiking and small town exploring. We appreciated the history of the property, as well as the sauna and stellar heating system in the depths of winter. Very clear directions for check in and amenities. We liked the pull out sofa bed as we are used to firm sleeping surfaces and were prepared for a small shower set up thanks to other reviews.

Bonnie’s home was perfect. Our group of 7 including 2 young children fit perfectly in the home. It’s to downtown Saugerties, and a short drive from all the Hudson Valley has to offer.

Perfect spot for a cozy winter escape. The clawfoot bathtub and wood stove (inside) + the fire pit and wood sauna (outside) make for the perfect getaway. We loved all of the beautiful design features of the guesthouse (a-frame ceiling, exposed beams, original wide-plank floors), and tons of thoughtful touches throughout (well-stocked kitchen with lots of teas and coffee, drinks available to purchase, bluetooth speaker for putting music on, games, bathroom products, etc). Great location near Bartlett House and Art Omi and a quick drive from Hudson, Kinderhook, and other neighboring towns. Donna was super helpful and welcoming. Thanks for a great stay!

We had a wonderful escape from NYC at Tim's place. Beautiful view. Home was as described in photographs. Many interesting books and artwork. Well equipped kitchen. Tim also provided an extensive list of things to do in the area. Would recommend to anyone who wants a peaceful and private getaway.

Vicky’s listing is the perfect getaway for a couple. We loved the proximity to downtown Rhinebeck. Vicky was flexible with our needs and extremely responsive and friendly.

We had such a wonderful stay! The kitchen was incredibly well-stocked with pots, pans, and all the cooking equipment we needed—it made preparing meals so easy and enjoyable. The snowy weekend brought stunning scenery, and we loved just sitting by the windows, soaking in the beautiful views. The fireplace was a huge highlight! There was plenty of firewood and clear instructions to get it going, making for such cozy evenings. William was fantastic—super helpful and quick to respond to any questions we had, which made everything smooth and stress-free. This stay was everything we hoped for and more. Highly recommend! 🌟

Miles and Ruth were so kind, helpful, and responsive during our stay. The house is perfect for a big group with plenty of spaces to hangout with a big group or find a quiet spot to yourself. Our group had the best time cooking in the large kitchen, relaxing by the fireplace, and in the hot tub.

Olia was a fantastic host and was super diligent in making sure we had everything we needed. The house was beautiful and spacious and my family loved it. There were plenty of activities and things to do around the house and we all had such a fun time. Would definitely consider coming back in the future!

The house and the barn were the perfect spot to gather family scattered between Baltimore and Albany. We had planned on visiting Art Omi but the weather didn’t cooperate, but the house was such a lovely space that we had no reason to leave! We even got a little show from two adult and one juvenile bald eagles! Lovely home, would absolutely recommend!

Overall the place was very nice to stay at. Hosts/Property manager were EXCELLENT communicators (we had an issues and they had solutions within 30 minutes). Close to supermarket (right down the street), along with close to being downtown Saugerties, resturants and getting on the thruway. Would recommend for families.

A great get-away. Super comfortable, just as advertised, and with an incredibly stocked kitchen. Our dog had a blast romping in the yard, and my wife and I are already talking about going back in the summer. We loved it.

We had a terrific stay. The house was exactly as advertised.

This property was perfect for a weekend get away for our group of 11. The setting is beautiful and provided opportunities for us to get outside and go sledding, do short walks, play ping pong and jump on the trampoline. The house was spacious enough for our group. The centerpiece is the kitchen which served as our hang out place as well as for eating and cooking. Rhinebeck is a cute village that is close by for shopping and eating out. We also enjoyed going to some local parks for more extensive walks. I messaged several times with Alina who was very helpful in answering questions about the house. We got snow our last night and she made sure that the driveway and walk ways were clear in the morning and allowed us a later check out because of the storm. All in all a great house!

Wonderful condo - so easy to communicate w Dawn. She is resourceful and helpful! The condo unit is an end unit with the ability to walk to the ski resort as well as the Country Inn hotel. Husband used the hotel hot tub and said the hot tub was great. Pool was good too - outside pool in the winter is always a treat! Lots of bedding options in the condo - one of my teenagers slept on the couch and said it was amazing. Full kitchen capabilities and good coffee maker. :) Thanks again for a great weekend escape!

We spent two wonderful weeks in Diana’s property. We were close to anything we needed. Very quiet and safe neighborhood to walk around. Diana is very responsive and gracious host. We can’t wait to come again.