Family-friendly holiday rentals in Cragsmoor

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!

My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.

Hidden gem. Really appreciated the countryside accommodation. The hot tub was nice and hot and we enjoyed a fire right after. The stores were in a close enough proximity if needed. My fiancé was skeptical as it’s right next to another property but we had are own space and we were not disturbed. Also we enjoyed the fresh eggs and being able to bring our fur babies.

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!

Perfect location — it’s directly in the middle of Minnewaska State Park and downtown New Paltz. Stargazing in the hot tub was a perfect way to relax after a long hike.

beautiful place, friendly owners, everything you need to disconnect from a crazy world

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.

Porter & Sara run an amazing cabin. Their container cabins are well equipped for a fun, romantic stay. The layout of the cabin lends itself to a warm welcome and the positioning of the couch, bed, and table make perfect use of the landscape - all facing the beautiful pristine meadow that hosts a ton of wonderful sights including deer, flowers and interesting insects! One thing that stood out was the lack of mosquitoes. Given the clearing and the amount of other wildlife, we were pleasantly surprised how comfortable it was to stay outside and not worry about being eaten alive. There are plenty of lounging accommodations, from nicely kept hammocks, to comfortable lounging chairs to a lovely hot tub . The low lights outside make the hot tub and patio a fun place to hang all night. When getting into bed, you’re greeted by the beautiful stary night. It was amazing to lay down and feel like we were all alone in the woods. We will absolutely be coming back for another romantic adventure.

Jacquelyn was very responsive, proactive, provided clear instructions and her place and linens were very clean! If you love farm animals, you’ll enjoy this place even more as she allows you to visit her farm.

We enjoyed the lovely cozy, private cottage with our family. It was a pleasure to have the animals nearby for the kids to interact with, a safe environment to roam in the woods, and very convenient to have the farm shop a few steps away for local eggs, meats, etc. The cottage was stylishly modern with a clean aesthetic and modern conveniences. Josh was very accessible via text/phone and checked in with us during our stay. We enjoyed ourselves thoroughly and would recommend to nature lovers, families, and those looking for a getaway in the woods!

Donna's place was amazing! We knew we would love it from the pictures but were even more blown away when we walked inside. It was the perfect cabin with every amenity and more that you could want for a remote get away in the Catskills. We went up with our dog and loved every minute - will definitely go back for our next trip up!

We had the best time staying at this cozy cottage, very comfortable with an awesome view! Kitchen had everything we would need. Great hospitality from Wayne and Renee! We can’t wait to come back again soon

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.

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!!

Really cute place. Comfortable beds and Sofas. The propane fire place was ideal. It was cold and icy when we stayed and we pretty much stayed in the whole time. It felt very warm and cozy. John was very responsive and helpful, he made the whole experience very easy for us.

Easily one of the nicest little cabins around. Can’t beat the privacy / grounds with Mountain View’s. There are nicely landscaped walkways and paths all around. We also appreciated the convenience of firewood and drinks for purchase on the property. Great location for hiking, snowboarding, fishing, not far from breweries like west kill, and towns like Woodstock. Paul was a great host who was very responsive to any questions we had. Will definitely book again.

Cute house, open concept first floor was great for a weekend with our girlfriends! Hava was very responsive and kind!

Everything was exactly as was stated and it met the expectations and more. Would recommend anyone to stay and if I ever return will definitely rebook.

We were absolutely charmed by this stunning house, surrounded by breathtaking nature and offering incredible views—especially over the lake. Every corner is filled with character and warmth, making it feel like a true hidden gem. A huge thank-you to our wonderful host Sandy, who was incredibly thoughtful and proactive throughout our stay. We couldn’t have asked for a better experience. We’ll be back without a doubt!

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.

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.

Three friends met at this beautiful carriage house with the feel of a French chalet! We stayed two nights with varied weather conditions. The house, grounds and location was perfect. Hot tub was used and so relaxing. The surroundings were beautiful and peaceful. The host, Diane was very helpful and friendly. What host makes scones each morning and delivers them warm?! Visited the Ashokan Reservoir trail, Opus 40, and Woodstock. Recommend this home highly. You won’t be disappointed!

Stayed for a weekend with my fiancé and dog. The studio was clean and spacious and included everything you might need. The property was beautiful, scenic and tranquil - and the pool was a definite highlight! The location was ideal as the town of Woodstock is just a quick drive away, which created a perfect balance of privacy and convenience. Definitely recommend and would love to return again.