Kid-friendly vacation rentals in Olive

We had the best time at Lapla cabin! We always stay somewhere different in the area and this is one of the best spots we’ve stayed. Our pup absolutely loved the woods and stream, and it was great to have the natural barriers around the property so we didn’t have to worry about her. Both the property and the house were so peaceful — I loved the gas fireplace (so easy to use on chilly mornings) and the sounds and view of the small waterfall in the creek from the living room window. Amazing.

Kates place was absolutely perfect for our weekend getaway! We enjoyed hiking in the area, a friends wedding and just the quiet in the mountains. Would love to stay again!

Really great space! Our dog absolutely loved playing fetch on the front lawn, and I was very pleasantly surprised by the sauna. I’m normally dubious of Airbnb saunas, but it was spotless, new, worked perfectly, and was a real surprise and delight of the stay.

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!

Jane’s home is beautiful, quiet, and so relaxing. The area itself is wonderful and quaint and the home has everything you need and more. We sat out each morning on the front deck for coffee and each evening for a glass of wine, and ate dinner on the screened-in porch. Despite the temperatures reaching 90 degrees outside, the home remained very comfortable even without A/C. There were plenty of fans and the evenings were pleasantly cool. Jane is very friendly and helpful—stopped by on our first day to give us some wonderful local recommendations (our kids loved visiting a nearby apple orchard / restaurant). Honestly, you can’t ask for a better host. We already miss the place and would definitely return!

We had such a wonderful stay at this home over the weekend! Communication with the host was seamless from start to finish — Erika were responsive, helpful, and made everything easy. The house itself is cozy, beautiful, and truly feels like it was built and cared for with love. Every detail, from the décor to the layout, made our family feel comfortable and right at home. We would absolutely stay here again and highly recommend it to anyone looking for a peaceful, welcoming getaway!

Monika's home was one of the best airbnbs we have ever stayed in. The design, style, and quality is something unparalleled in other airbnbs, it has a cohesive, elevated design throughout the entire home. It has everything you could possible need and is so thoughtful in every way. The backyard is huge and is perfect for a family to spend time together. We went on a great hike to a waterfall (which is within walking distance). Location is amazing as it's a close drive to Minnewaska. The location in Kerhonkson is in a nice secluded area. If you're looking for the perfect place to stay in the area this is it!

Beautiful and quiet. Lovely area

We had a great experience staying at Corryn's loft. It was clean and comfortable. In the future I will plan on staying in the suites higher up in the building though. This is out of the hosts control, but the other guests were not respectful of the other guests staying in the building.. So higher up in the Strand house is the way to go!

Nichole’s place was perfect for crashing for a night after a birthday party nearby! We were very comfortable and all necessities were there.

Miryan's home is exactly as described, she was a wonderful host and went above and beyond any expectations you could have. It was a pleasure to stay at her home.

The Modena House was perfect for our trip. We wished we had the chance to enjoy the outdoor aspect a little more, however time and weather didn’t cooperate with us. The place is adorable, a great kitchen, nicely decorated sitting room, bathroom and bedroom made for a lovely stay. The hosts are top notch! We hope to stay again in the future if we are in the area. Xoxo

Worth every penny. Lisa was super responsive, the space was so welcoming and the surroundings were gorgeous. It was exactly what I was looking for in a little home away from home getaway.

Such a fantastic stay right in the heart of Kingston! This apartment was exactly as described and incredibly clean. Easy to get to everything in and around Kingston. Tara was a responsive host with clear instructions on how to check in/check out.

The place was nice and roomy. Very accommodating. Sarah was fantastic at responding to getting us a coffee pot of which the place did not have one. That was so much appreciated. I hope her future guess will appreciate that also.

We were in the area for my daughter's college graduation, and the "shack," as it's known, was perfect for us. It's comfortable, well-appointed with cool amenities (big, super-comfy bed, full bathtub, lots of vintage fixtures and furniture and a woodstove). What's really cool is that the dwelling's modest facade belies a remarkable spaciousness once you get inside - like the Charmed Wizarding Tents in "Harry Potter and the Goblet of Fire." It's sort of a loft, with small spaces above in the front and rear, but the real attraction is the cavernous space in between. It's quiet, but surrounded by restaurants and other small businesses and a small park that hosts a farmers' market on Sundays. Don't miss the standout cuisine at Garden House, the Middle-Eastern restaurant right across the lane. It's a hub for a small, sweet community of older folks who add real warmth to the place, and the food is incredibly good. Comfort with a sense of adventure. Would we stay here again? Definitely.

This condo is absolutely beautiful and comfy! We especially love the bed and pillows.

Beautiful gem, fantastic hosts. Wouldn’t change a thing. Thank you!

Luiza was a wonderful host. She provided detailed check in and out instructions, as well as local recommendations for our stay. Her place was exactly as pictured and cleaned wonderfully for our arrival. We hope to be back for another ski trip!

I highly recommend Suzanne's place for anyone visiting Windham! She was incredibly responsive and helpful throughout the booking process and my stay. As someone who travels constantly for work, my schedule can be quite unpredictable, and Suzanne was unbelievably accommodating and flexible with my changing needs. I truly appreciated her understanding and willingness to work with me. The location is fantastic, right in the heart of Windham, and the view of the ski resort from the back deck was an unexpected bonus! I only wish I could have stayed longer. I'm already looking forward to my next visit, not just for winter skiing, but also to explore the beautiful surroundings throughout the year.

Was as advertised. Would recommend

Dan’s place is cozy, comfortable and just minutes away from Mt. Beacon in one direction and ten minutes away from Main Street in the other direction. The kitchen is stocked with cooking essentials, though there are so many delicious restaurants nearby- the best of both worlds! The bed was extremely comfortable and the jetted bathtub was a huge bonus. I genuinely relaxed there, which is a rarity for me. Thanks so much, Dan!

Great host, responsive and accommodating! Place was clean and felt right at home away from home! Check in and check out was easy, parking on site, nice neighborhood, cozy place, will definitely be staying here again!

This condo fit our needs perfectly. The walk to the mountain seemed further than it was good value sauna was a nice touch would stay again