Family-friendly holiday rentals in West Stockbridge

Absolutely loved this house and its incredible energy! The blend of old New York and Parisian charm creates such a unique and inspiring atmosphere. As an artist, I felt truly energized and creatively inspired during my weekend stay. Every corner of the home has character and warmth, making it a perfect retreat. Highly recommend to anyone looking for a special and memorable experience!

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.

Michael and Enrique were excellent hosts, and left me and my girlfriends ice cream in the freezer to enjoy! They responded quickly when we had any questions. The view from the hottub looking out onto the woods is beautiful and the hottub was just what we needed to relax. A beautiful, cozy getaway, and so close to Rhinebeck!

Loved the house. Kitchen is great. Awesome living room with very comfortable couch and fireplace. Bedrooms perfect. Hot tub was perfect. Original Nintendo system upstairs was fun. Went skiing at Hunter which is 20-25 min away. Woodstock 15 min away. Really a great place. Jaime was responsive, friendly and helpful.

Amazing cabin , close to everything, clean ,

I had a wonderful stay at Jackie’s Airbnb. The space was clean, comfortable, and exactly as described. Jackie was a gracious host, providing clear communication and thoughtful touches that made my visit memorable. I highly recommend staying here and would love to return in the future.

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.

Place just as described . Sadly only had one night here, we could happily of stayed the week. Place was exactly as described. Great communication from host, place was very clean. We requested an early check in and despite some wintry weather they made it happen. It was lovely to arrive and the wood stove was already lit and fire roaring for us. We did not have the time to hike but this looks like the perfect location to begin and end a hike. Due to lack of time we cheated and drove to the Tibetan Monastery which is well worth a visit. We will be back!

Super responsive management of property. It was a very rainy weekend, so my daughter and I really enjoyed the large TV with the option of many streaming channels. Bed was comfortable and the place was neat and clean. Fantastic location as well.

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.

Super close to town! Lovely setting. Fun to take a shower under a skylight. As others have said, it’s very compact! Would be an ideal place for a person to get away to write.

Lovely place in Saugerties, close to lots of great hiking and restaurants.

Donna's place was a wonderful weekend stay! Beautiful property and guest house. Well appointed and care for. Just a few improvements that would have made our stay even better--a small microwave for quick reheating of coffee/leftovers, a luggage rack and place to store/hang clothes, and ensuring the driveway and a walking path are cleared of snow even when out of town (with thawing and refreezing, we had to navigate two inches of solid ice, which was terrifying both on foot and in the car).

Scott's place was great. We were so relaxed and felt right at home. We will be going back which is the best compliment I can give an AirBnB. The views were beautiful!

A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

Vicky’s charming Airbnb is a perfect getaway! The space is attractively decorated with thoughtful touches that make it feel warm and inviting. The kitchen is impressively well-stocked, making it easy to cook and enjoy meals at home. The bed is super comfy, ensuring a restful night’s sleep. Best of all, the location is ideal—just a short walk to the charming village of Rhinebeck, where you’ll find great shops, restaurants, and cafes. Highly recommend!

This was our second year staying here with friends, and we had such a lovely time. There's plenty to do inside the house itself even on a dreary day, with curiosities and art abound, instruments, games, fireplace, etc, a great kitchen for group meals, and spacious and comfortable rooms otherwise. Olia is very kind and responsive, with plenty tips for the local area. We'd recommend for groups or families in an instant. Nothing like relaxing in the hot tub while looking out at the mountain vista with rain pattering on the porch roof above - pure bliss.

My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

Such a beautiful winter getaway, my bf and I came here for VDay weekend. We loved the private quiet area for just two of us the space was perfect. Can’t wait to come back in summer to utilize the natural pool.

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.

We loved celebrating my wife’s birthday at Tina’s home with our bichon frisée! Her home was so peaceful and we loved relaxing in the soaking tub, listening to music, and unwinding. It was the perfect weekend for staying in and reading books while surrounded by nature (and rain!). The home was easy to find and had everything you could need for a snuggly weekend in. We loved Red Hook - we have never explored it before! The shops are adorable. We hope to be back when it’s warmer to try the pool!

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

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.

We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.