Family-friendly vacation rentals in Greenwood Lake

Such a beautiful spot on the lake!!! We had the most beautiful weekend, the kids loved he pool and the boats, nothing was missing! We would have stayed another week! Jennifer and Jose answered all our messages within a few minutes and were super accommodating. We will definitely be back!

This is our second time staying here and we’ll definitely be back for a third and hopefully fourth time! John’s place is peaceful and the amenities make it feel like a true vacation. John is super responsive if you need anything.

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.

My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!

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!

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.

It’s a really sweet location on a working organic farm. The stairs to get to the loft are definitely for the agile, but otherwise it’s a nice little lay-out.

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.

Mahmoud was a wonderful host. Very responsive, pleasant, and helpful. His home and the views were spectacular, and the koi pond was beautiful. It’s a great location to stay while visiting West Point, as it’s a quick drive across the Bear Mountain Bridge. Our large group felt comfortable and welcomed. One of the bedroom descriptions could have been listed a little clearer because you need to pass through the master bedroom to get to it. Luckily our family was ok with that. We would stay again.

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 had a very peaceful stay on Julia’s beautiful property. We were able to check in early, which was very helpful to us. Julia was very responsive when I messaged her which we appreciated. The Little House had everything we needed and would highly recommend!

This place is truly a gem! We enjoyed swimming in the waterfalls and relaxing under the trees. We can’t wait to return. The house is also lovely with lots of interesting and quirky touches that we enjoyed. Incredibly well stocked kitchen and everything we could want!

We have stayed at Erik's place 4 or 5 times now. It's perfect, has everything you need. It is centrally located to surrounding towns. Erik and his parents are very friendly and always responsive. I highly recommend staying there!

We had a wonderful stay at this house. It was clean, spacious, very warm despite the cold, and had a terrific pool table and air hockey table. Our family relaxed and spent good time together.

The place worked perfectly for what I had needed. Travel a lot for work, and this time my wife and son came to visit for a few days of the stay. Host was very nice and helped us with accommodations and recomendations of local eateries. Very much enjoyed our time here, would stay again.

A Perfect Weekend Getaway! We had such a memorable stay at this alpaca farm! From the moment we arrived, the owners made us feel right at home — they were so kind and genuinely conversational, which set a warm tone for the whole visit. The alpacas were definitely a highlight — such a unique and charming experience, especially for my daughter who absolutely adored them. It’s not every day you get to hang out with alpacas in such a relaxed and welcoming setting! The pool, hands down, was our favorite part — clean, refreshing, and perfect for unwinding. The ambiance throughout the property was peaceful and serene, exactly what we were looking for. We stayed in the carriage house, which was spotless and beautifully maintained — cozy, quiet, and perfect for our little family. Overall, we had a great time and would highly recommend this place to anyone looking for something a little different, relaxing, and full of charm. We’re already looking forward to our next visit!

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.***

We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

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

It was comfortable, very roomy, and cozy. There was good shared space and good privacy. The grounds were lovely, there was a great pool, and it was very convenient to so many good things to do in the area. It's one of our favorite rentals to date!

We loved staying at Bill's beautiful home! Truly even more gorgeous in person. Bill was friendly and communicative. He asks renters to sign an additional contract, but all his requests were reasonable/standard airbnb rules. The house is comfortable and spacious and the surrounding area is absolutely beautiful. It's a speedy drive (3 min) to the main street of Woodstock -- restaurants and shopping galore. We cannot wait to come back and stay again!