Kid-friendly holiday rentals in Olive

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.

Top notch experience and accommodations. Michael was the most responsive and organized host. Perfect retreat for a long weekend. Amenities (hot tub, fully stocked kitchen, fireplace) and location (short drive to Woodstock) make this a really special place. Hope to be back soon - thanks for the best hospitality!

We were looking for a quiet place surrounded by nature, and Rick’s house was exactly what we needed. The home sits right by a small creek, making it incredibly peaceful—waking up to the calming sound of the water was a real highlight. Everything was clean and in good working order, including the cozy fireplace. We truly enjoyed our stay and left feeling well-rested. If you’re looking to disconnect from the fast pace of city life and immerse yourself in nature, I would definitely recommend this place!

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!

Beautiful and quiet. Lovely area

Beautiful place, we loved the hot tub, the fire pit the gorgeous bedroom and fully stocked kitchen. A dream to cook and hang out in. This is a place you want to stay in and not leave. Internet and wifi was excellent. Communication was great. The projector system didn't work at all and we did get some help, and when they weren't able to help they offered us a free night stay if we wanted to stay another day. However, please stop with the AI responses they are not helpful and just make it feel less responsive once you realize it's not a human. Cons were just that the sofa isn't very comfy or loungeable, but that's really it. Thanks for a lovely stay!

Very comfortable home. We loved sitting on the porch, listening to the sound of Stoney Clove Creek, or relaxing around the fire pit out back. On one rainy day, we had a fire in the wood stove, which made the living room very cozy. The kitchen had all the things necessary to prepare meals, and I particularly enjoyed the three different methods for brewing coffee that were made available. Wow, what a lamp collection! I highly recommend this property for those who wish to enjoy all the Catskill Preserve has to offer.

Cute, cozy, clean, and super close to the bike trail! Perfect stay for a weekend exploring the towns along the trail.

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.

We had a great time at the Catskills and enjoyed our stay comfortably at the Catskills Village. We didn't bring a car and were able to explore the town by walking and Ubering to Hudson (with a wait time, as expected). Tommy and Jenna gave us some recommendations, which made planning for the trip easier. The space was perfect for two, with the bathroom on the second floor and the bedroom on the third floor. Everything was as described (we loved the interior design!) and perfect for a weekend getaway. Great location for a peaceful time away from the big city. Thank you Tommy and Jenna!

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

Carmen's place is an amazing getaway. Set back and quiet, but close to town. Very clean, and with all the amenities you would need. Very responsive to all questions leading up to the trip. 5 stars all the way!

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.

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

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

Great Airbnb! Great Host! Perfect for visiting West Point

Host was responsive, place was tidy and instructions to get in and out are very clear. Place had an adequate lot as well and is also very peaceful

Cozy apartment, walking distance from the water front. Had a great weekend getaway.

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!

Gerry’s place was a great, quiet stay for us. Close by to Kaaterskill and many other Catskill mountain attractions. Gerry was great at communicating and went out of his way to be helpful with our checkout procedures. I would definitely stay here again!