Family-friendly vacation rentals in Woodbury

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!

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

Paul's place was just as described. My husband and I had difficulty figuring out the thermostat and he was quick to reply to our request for help. The pool and hot tub were great! Very comfortable bed.

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!

Cozy cabin in peaceful surroundings. Place had everything you need. Communication with host superb - responsive and helpful. Enjoyed our stay.

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

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.

Very nice house, good fishing and wildlife nearby. A little closer to the neighbors than expected, but overall a great place and would love to come back

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 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!

The perfect spot to be nurtured by nature! The sweetest cabin had everything we could need and gave us the ability to unplug, relax and rejuvenate. Loved being able to go hiking and just enjoy being outside.. surrounded by gorgeous nature. The babbling brook was so soothing. Honestly, just a perfect spot to enJOY!

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

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 was a last min stay and Joe was able to make the accommodations needed! Looking forward to booking again!

Billy and Rhobin were so helpful and easy to communicate with. The house was so comfortable and peaceful. The property was lovely! 5 Stars all around! Thank you for a fantastic stay!

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

Myself, my partner and our two fur babies loved Julia’s! The “little house” was our home away from home for a few days! It was the most quaint and tranquil cottage for my family to recharge! We had two nights of deep sleep as the bed is like a cloud! My partner took full advantage of the porch swing, clawfoot tub and our girls loved the ample acreage and privacy the little house provided. My family also loved our time poolside. It was tidy, clean and private. It was truly a place to have your morning coffee with zen! Julia was very accommodating to our needs throughout the stay, hospitable and responsive. We go out of our way to find privacy and somewhere that’s great with our fur babies. Julia and the little house delivered just that- We would highly recommend any stay with Julia and to experience this property for yourself!

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.

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.