Family-friendly holiday rentals in Cold Spring

We had a wonderful time at this place for our mini moon. It was relaxing, beautifully decorated, well stocked with everything you need! The hosts were very responsive. We would stay here again in a heartbeat! For anyone coming from NYC we stoped at Pho Tibet in New Paltz for lunch on the way home and the food was amazing!

Abagail was very helpful in getting settled. The house is full of interesting antiques and paintings. There was a wonderful view of the Litchfield Hills and a lot to do outside. It is rustic but it has every convenience of home. Great shower. Must have been a barn but now it is a museum of Art Nueveau treasures and stained glass. Very peaceful and slept great.

We had a great time fishing and going to local farms! The hosts were great! They even got us some night crawlers and helped find a hat we left & ship it back!

We had such a great stay at Eugene’s place! The house was perfect for our group — spacious, comfortable, and full of fun things to do. We especially loved the private theatre, the hot tub, and especially the sauna — such a great touch! The volleyball net was a hit, and there were tons of games in the closet that kept us entertained. The kitchen was well-stocked and roomy enough for us to cook meals for our large group, and there were plenty of different areas to hang out in, everyone could find their own space to relax. The towels were plentiful (huge plus) and having access to the washer and dryer came in handy during our stay. Eugene was a fantastic host — super friendly, very responsive, and just really helpful all around. We also got to enjoy a few deer sightings right in the yard, which felt magical. We visited the nearby alpaca farm and did the Beer Mountain hike, which was a nice outing. All in all, a wonderful stay. Would absolutely come back. Thank you Eugene!

We keep coming back to stay here because the house is so cool and has everything you could need! A great getaway outside of nyc anytime and we always recommend to others.

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Julie's place was the perfect winter getaway. The fireplace, hot tub and sauna warmed us and the very well-equipped kitchen enabled us to prepare great meals. The house was beautiful, with two living rooms for different activities and energy levels, a game room downstairs, a dining room with a large table and chairs, and comfortable furniture and beds throughout. Julie texted me to make sure that our every need was met. We had a snow and ice storm, and she had the driveway and walkways plowed, shoveled and sanded twice, and kept plenty of salt on-hand. We hope to return sometime in warmer weather so we can enjoy the pond, too.

We had a nice time staying. It has a Well stocked kitchen. It is near to grocery and shopping in Stone Ridge. It has Great fireflies at night and a good view of the sunset.

We had a really lovely stay at this cabin in Boiceville. It rained every day during our trip, but honestly, we didn’t mind—it made the space feel extra cozy. We spent our time relaxing indoors, reading, cooking, and just enjoying the slower pace. The cabin was clean, comfortable, and had everything we needed. It was tucked away enough to feel peaceful, but still a short drive to Esopus Creek and Phoenicia, which we enjoyed exploring when the rain let up. The host was helpful and easy to communicate with, and everything about the stay went smoothly. If you’re looking for a calm, quiet retreat in the Catskills—even on rainy days—this spot is a great pick.

Would absolutely stay again! Really loved the way they've updated the space but kept the classic touches of the house. Huge well appointed kitchen with everything you could need. Peaceful outdoor space with lots of privacy. And overall a very spacious house that feels like you could have a big group without getting in each others way. Ryan & Lauren were super on it. Will definitely recommend to friends.

Location was great and close to town. The home was very clean and fully stocked. Annemarie was very responsive and accommodating. Great stay!

We loved the place, it was a beautiful home with lots of light and accessible green space. It was perfect for a short getaway. It’s a short drive from nearby towns and was very easy to find based on the directions. Mark was a responsive and accommodating host and we had a wonderful time in his airbnb.

Really enjoyed our stay at this peaceful farm. The location was very convenient to Bear Mountain State Park / the Appalachian Trail. The sound of the frogs at the nearby pond and the friendly horses really make this place a gem. Would highly recommend for a relaxing getaway!

We spent the weekend in the area and Tim’s place was fantastic. It’s loaded with charm, comfortable and very well appointed and stocked (right down to treats for the dog). The location is beautiful and the views are amazing. Can’t wait to return!

Beautiful chalet with even better views - perfect for a calm and peaceful get away from the city, near hiking trails and 7 min from town for restaurants, had a great weekend and hope to be back soon

This place is like heaven!! Charming and beautiful views of Greenwood Lake. The beds were super comfortable and the place was well equipped with everything you could need. Great communication with our hosts. Highly recommend this place!!

My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.

This A-frame escape was exactly what I needed — the perfect break from the city. The place is beautifully designed, cozy, and filled with thoughtful touches. The jacuzzi was absolutely incredible, especially under the stars at night, and the A-frame structure made the whole stay feel like a peaceful retreat.

Loved this little studio! If you’re doing anything at Mohonk preserve (we did Rock the Ridge), it’s minutes away from Testimonial Gateway and Ulster County Fairground. New Paltz is just down the road with stores, cafes, and more. The apartment is cozy but functional and the kitchen is setup well. Perfect for 2 people, couple or friends. Bonus — I rented an EV and was stressing about getting it charged but Franky offered to let me charge it overnight, which was a life saver!

This is a beautiful place. Second time we’ve stayed there and I would like to come again next year!

My wife and I had a great stay at Paul’s place. Very clean and just as described. Look forward to staying again in the future.

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼

Amazing amazing for a birthday weekend. Good proximity to Hudson while still feeling in the woods. So clean and cozy.