Family-friendly holiday rentals in New Fairfield

You feel secluded and private - everything you need to stay in - but also minutes from Woodstock and great restaurants. Beautiful views! Very romantic vibes, especially in the winter. The host was super helpful with communication about the weather. We got lots of snow and ice while there, and they made sure the steep driveway was well plowed and sanded for our departure.

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.

We had an amazing stay! The setting was absolutely beautiful, with stunning views and a peaceful atmosphere. The space was impeccably clean, which made our stay even more enjoyable. One of the highlights was the hot tub – it was the perfect way to unwind after a day of exploring. The host was incredibly responsive and saved us with a last-minute booking, which we are so grateful for. We couldn’t have asked for a better experience. Highly recommend!

House was spotlessly and thoughtfully decorated. The bed was comfortable and hot tub was absolutely phenomenal. Skylights let in beautiful natural light for reading and relaxing. Michael and Enrique were proactive about reaching out beforehand with the house information and we really, really enjoyed our stay. We're not used to baseboard heating so some of the noise from the heating surprised us, but that's to be expected with any place that's not your home. Would gladly stay here again.

The house was lovely just as advertised. It was nice to get away into the woods and enjoy the hot tub.

Had an enjoyable stay at Ralph’s Woodstock location. Ralph was accommodating regarding the hot tub, as it was not working during our stay- We really appreciate it! The area itself was secluded and peaceful. The town of Woodstock was super cute. A great place to relax and unwind!

Amazing cabin , close to everything, clean ,

Linda's place exceeded our expectations! Staying there was the perfect cozy weekend getaway. The landscape was covered in snow, creating a breathtaking view that we enjoyed from almost every part of the house. We can't wait to return in the summer to experience its beauty in a whole new way!

John and Lizz's place was the perfect blend of spacious yet also cozy, with many of the rooms leading to the open main living room with lots of light. It was the perfect place to spend time with a larger family or group of friends. The beds were comfortable, and everything was clean when we got there. Would definitely stay again when in the area!

Nidhi is an amazing host with an amazing place! The house itself is beautiful and the vibe is peaceful! We went in a winter night, sat by the fir pit, enjoyed the sound of the stream. And when we needed comfort the beautiful warm house was right there. Best of both worlds nature and comfort together. And the next morning we were just 15min drive from Woodstocks main street. I highly recommend the stay. It was an amazing experience

Traveled back to this area for several New Year’s celebrations. Extremely convenient to Buttermilk Falls Farms and nearby restaurants. Will stay here again in the future.

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.

Our second stay here - we’ll be back again soon. Kind, responsive hosts and an incredible property for great value.

I am so glad that I found Yvonne's place. It was perfect for my group. Clean, tons of beds, laundry facilities, and a great kitchen that enabled 9 or so of us to cook dinner for a group of 20. We were so thrilled to learn there was a propane grill with propane in it, ready to go. The beds were comfortable. The showers provided plenty of hot water. The living room was comfy and cozy with nice couches that were comfortable enough to sleep on. I would stay here again and again if the opportunity arises.

Despite booking my stay with three other friends for my birthday during February, it was the absolute best decision. Everything was as described, lot of great in-home amenities including games (i.e. ping pong, pool, tons of table-top entertainment.) Scott was absolutely one of the best hosts I have coordinated and communicated with. He would check-in to ensure we had what we needed and when there was a heavy snowfall the evening prior to our departure date- he immediately checked in and had the walkway and driveway cleared of snow. Lot of great, beautiful hikes in the snowfall and do hope to have the opportunity to return during the warmer season. Thank you, again, for the wonderful accommodations and for being such a proactive and communicative host!

THE home in the country I've always dreamed of! No need to leave this house to feel like you're on vacation- everything is here. This place would be great to stay in during any month of the year. Amazing views from every window coupled with all kinds of interesting collectibles, books, toys and furniture inside. Super comfy beds. Doting hosts that make you feel pampered while simultaneously being unobtrusive. Perfect getaway for our very small family!

Nice and clean house with a hot tub that is well maintained! Getting into the driveway was a bit scary due to the weather and plumbing is a bit finicky but we had a great stay overall and the owner was very prompt with responses!

Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back

We absolutely loved our stay here! We brought our dog, and he spent hours gazing out the beautiful windows into the serene backyard, where we spotted birds and even some deer wandering by. The property was stocked with everything we could need, far beyond what we've experienced at any AirBnB. It was impeccably clean, incredibly comfortable, and so peaceful. Plus, it’s centrally located, just minutes away from great restaurants. Susan was communicative and made the check-in and check-out process super easy. We would definitely stay again!

We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

A great get-away. Super comfortable, just as advertised, and with an incredibly stocked kitchen. Our dog had a blast romping in the yard, and my wife and I are already talking about going back in the summer. We loved it.

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

Our 2nd stay at Elizabeth’s house and it was as nice as our last visit. Our kids love exploring the home and property which has a wonderful view. The kitchen is well appointed for cooking. We especially enjoyed the stone fireplace to relax after skiing. Would highly recommend!

We had a wonderful experience at Lisa's carriage house! We were in town for a Bachelorette Weekend (9 women from all over the east coast) and this was the perfect home base for our trip. When we arrived, Lisa gave a tour of the property and house, showed me how everything worked, and provided very clear instructions and suggestions. She gave us a great recommendation for dinner delivery that evening and was exceptionally responsive and helpful for the whole weekend. We spent a day at Sojo Spa and enjoyed a great dinner in downtown Englewood on Saturday night. The house had everything we could have needed from an amenities perspective and tons of warmth & charm on top of that. Thanks Lisa for having us! We had an amazing weekend celebrating the bride-to-be.