Family-friendly vacation rentals in West Stockbridge

The house was large and comfortable and the view was fantastic. We had a wonderful time here. There was a fireplace/peat stove in the living room, and it added both heat and ambiance. The couches were cushy and comfortable. The hot tub was a highlight and we were lucky to be there for the full moon. We were a 15 minute drive to Chatham which was charming with a bookstore, restaurants, bakery, coffee shops and a consignment store. We didn't check out everything that was there. If you're looking for an activity, I highly recommend the Hancock Shaker Village.

Myryah’s beautiful home was a peaceful secluded getaway. The home was spacious, cozy, and filled with sunlight throughout the day. The fireplace was perfect once it got chilly at night. The hot tub was clean and was the perfect way to relax as you’re surrounded by the forest. I loved that the home had a record player and a sound system. They had a great collection of records, but we also brought some from our own library to listen to during our stay. The home is perfect if you also have kids. Our son loved it here. We would love to stay here again in the future, highly recommended!

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.

Really enjoyed our two-night stay at Michael and Enrique’s place! They provided lots of clear instructions ahead of time and the place was quite easy to find. Their home is very well laid-out and cozy, and our dogs loved it too. Enrique is very communicative throughout. We will be back!

We really enjoyed the long weekend at Jaime’s place! The house is even more beautiful in person than the pictures with so many nice details. Jaime has thought of everything to make this home a great retreat. Felt immediately cozy and at home. We loved all the amenities- the hot tub, sauna, fireplaces, Sonos, Nespresso, TV, Nintendo classic (wow that was a fun surprise!), board games, fully stocked kitchen and amenities in all the bathrooms. We also loved the vintage rugs and amount of cozy nooks to relax in. Beds were comfortable and had ample space to spread out if you’re a large group. Lots of room to unpack and store your belongings in the closet. Everything in the house easy to operate and Jaime’s instructions were clear and was easily available for questions. Would love to return in summer & try the pool. My kids loved spending time at this house. Great location and easy access to Woodstock, Kingston & Hudson and looking forward to returning! Many thanks Jaime :)

Very comfortable, relaxing cottage with nice outdoor space, natural setting, and only 5 minutes into town

We had a lovely, relaxing getaway. The home, river, trees, and hot tub are beautiful and soothing to the body, mind, and soul. Patrick and Fiona did a great job of communicating to make sure everything went smoothly. Very happy with our experience.

This is a beautiful location and incredibly close to town. The fireplace keeps the home toasty and is great after a soak in the hot tub. Check-in and check-out were seamless and everything was clean. The WiFi was strong and it is clear that these are seasoned hosts who know what they are doing.

We had a wonderful stay and Juliana and Paul were extremely pleasant, kind and responsive. Cozy loft was so lovely and I especially loved the antique chandelier. We had such a restorative time here and would absolutely visit again.

Great location, we could walk into town! Shower was too small for my husband but we made it work!

My family and I absolutely loved our visit to Karine's farmstay! The apartment itself was cozy, inviting, and clean and the farm on which it is located is incredibly beautiful. We greatly enjoyed the opportunity to interact with all of the animals on the farm and to rest in such peaceful surroundings. I feel as though we got an incredible bargain at this residence, and I would gladly stay there in the future!

Bonnie’s home was the perfect place to stay while we were in the area. Everything was just perfect and she added so many extras to make us feel at home. She was very responsive when we had questions, check in and check out were so easy and her instructions were clearly posted. We would definitely recommend Bonnie’s adorable home and hope to be back in the future!

Scott hosted my friends and I in a beautiful home on the water. We enjoyed water sport activities, even in November! We were 10 minutes away from New Paltz and 10 minutes away from hiking spots! The house was east to locate, check-in to, and Scott communicated very effectively. We were even granted late check-out! The house was very charming, well-stocked, and clean. One of my favorite touches was the “pet essentials” corner. Scott provided our pup with a bed, food bowls, and a leash - very thoughtful! His rules are clearly explained and easy to follow. I would definitely recommend a stay at Scott’s and would love to return next time I’m looking to stay in the area.

The cabin was cozy, well equipped & welcoming. Can’t say that I’ve ever slept on a more comfortable bed! The kitchen was well stocked with modern appliances. The property was certainly private, expansive & peaceful…maybe a bit too quiet for a Bklyn girl! A but tricky to reach and phone & internet service disappear as soon as you walk out of the house. The hosts were exceptionally responsive & helpful.

We always have a great time at this cozy cabin. It’s secluded, peaceful, and a great place to bring our city dog to enjoy nature.

Miles and Ruth are excellent hosts. I rented their property with many specific requests, and they found a way to accommodate me. I could not be happier with our stay and with the hosts. I highly recommend these hosts and this specific rental.

We enjoyed our stay so much!! It's a very unique home and Olia has been very flexible and communicative. We couldn't be happier. The best place to spend a cozy weekends among friends!!

Loved our stay at Amanda’s place. Highly recommended. The property was exactly as described—clean, comfortable, and thoughtfully equipped with everything we needed. Amanda and Kelcey were incredibly quick to respond to any questions, making the entire experience stress-free. I’d happily recommend it to anyone looking for a great Airbnb stay!

A beautiful house in a pretty central location. We are originally from the area and this house made us feel right at home. It’s clean, inviting, and comfortable. My kids had a blast too. Definitely recommend staying here!

Of all the AirBnBs my wife and I have been able to experience, Tina's is at the very top of the list—a place that's perfect for anyone looking for total peace *as well as* easy access to all the wonderful things that the valley has to offer on both sides of the river. Warm, exquisite, and anything but utilitarian, the property feels like a true home, with few if any traces of wear from previous visitors and much more on offer than most would expect from an AirBnB, including a fully stocked medicine cabinet, to give just one example. The next time we consider traveling to the region, the first question will probably be: "Is Maitopia available?"

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

Sunset Cottage was the absolute perfect place for us to spend a long weekend. The house is beautifully designed with modern touches like big windows with stunning mountain views. We loved the open lay out with the cozy living room and comfy beds in each bedroom that made it easy to relax after an upstate day. The cottage location is ideal with it actually being located in Woodstock vs many other airbnb’s that day they are but aren’t. We were just a 3 mins drive to Woodstock town where we had such good meals at Red Onion and Silvia, but felt far enough away to be immersed in nature. Each morning, we were greeted by a family of deer grazing in the yard! The house itself was incredibly clean and well-decorated, adding to the overall comfort and charm. The hosts were super friendly and gave us great tips on local hikes and restaurants. We're already dreaming of our next visit for a ski weekend or summer to use the pool!

This was our second stay at Dawn’s cabin. We usually visit the area in winter to ski but did a quick late fall getaway. We enjoyed Dawn’s recommendations for hiking and eating. We also enjoyed the pool and hot tub in the country inn and the fireplace in the cabin. The cabin has all necessary amenities and is well stocked! Dawn is an absolute gem! She is responsive and provides great recommendations. We look forward to our return in February to ski!

We spent three nights at Rich and Sheila's place and it was an amazing getaway. Our apartment was perfect-clean and comfy. We loved the proximity to the creek and the pool was a huge bonus! Rich and Sheila were both responsive and welcoming. We look forward to a return trip.