Holiday rentals with a pool in Olive

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!

Awesome property for a weekend getaway from the city. Sonny made this place into a fun playground - the pond is amazing, the hot tub, sauna, and back deck felt like a spa, and we enjoyed the fire pit and taking a short hike to the creek. The house itself is simple but has everything you need and we even managed to order Uber eats once from Kingston. The area is great, and we enjoyed the villages and a nice hike in the area. We will definitely come back.

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

We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!

The house is really gorgeous. Everything was very new/modern, clean, and comfortable. We enjoyed cooking meals in the kitchen overlooking the stunning view out the back. The hot tub and fire put were nice amenities to enjoy. The BBQ seemed to not be working, but other than that, no complaints. Location wise, the property is located in the northwest Catskills, near Stamford, NY, and convenient to many hiking spots in the area as well as nearby towns. The property itself its up on a hill, in what felt like a secluded and private spot, which made it feel like a real getaway and retreat. In sum, recommend this Airbnb for the nice amenities, modern touches, and amazing view.

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.***

It was a beautiful stay and everything were just like the photos! We enjoyed our stayed!

Our hosts have curated a beautiful and thoughtful space, with pleasing personal details, design and decor that made our stay easy, relaxed and met all of our needs for a quick get-away from city life…wood burning stoves for the fire-gazers, a well-outfitted kitchen for those of us who sought to cook as meditation, a crop of woods for kids to explore, a bilingual library for our bilingual readers etc. that rounded out the feasting of a holiday of Thanksgiving around the dining table. The house is near good food shopping, retail and restaurant culture etc. and could cause one to want to spend more time than a mere get-away in order to take it all in as well as enjoy the house itself; hence, we will have to plan to return-! Alex was incredibly responsive; the stove is beautiful, though somewhat enigmatic with its icons, and she offered to take time on her own holiday to walk us through it—and with one or two other minor questions she was patient and quick to reply. Merci Bien!

Loved this place. Very easy to find. The place is cute and co portable with good views from the main bedroom and living room. Very clean and tidy. Loved the stay.

We had an amazing stay at Kristen’s condo with our family—my husband, our toddler, and our dog. The location was perfect—secluded and peaceful, but still close to hiking trails and charming small towns. The condo was cozy, clean, and well-equipped with everything we needed for a relaxing weekend. Kristen was responsive and helpful, making our stay even better. Highly recommend for a family getaway!

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

My friends and I really enjoyed our stay. We hiked the devils path trail and Dimitry’s place was perfectly close to the trail and the restaurants around it. His place was great to go back to with a great shower and bath, a beautiful view and very cozy place, with coffee and a coffee maker. Very clean and Dimitry was responsive the whole way through and checkin and out was very easy. Would highly recommend and would stay again.

Very nice place with decent pricing. lots of room, clean, good communication from host.

We recently stayed at Andrew's condo, and it was nothing short of amazing! The location couldn't be better – right next to the slopes with easy accessibility to the mountain and the ski rental place. We were a group of two families, totaling 6 kids and 4 adults, and the condo was the perfect accommodation for our ski trip. The kids were thrilled with their bunkbed rooms, each equipped with their own TVs, providing a cozy and entertaining space for them to unwind after a day on the slopes. The condo itself was beautifully decorated, creating a warm and inviting atmosphere. There was plenty of room for all of us to relax and spend quality time together. The highlight for both kids and adults was undoubtedly the hot tub and pool. After a day of skiing, it was pure bliss to soak in the hot tub and enjoy the breathtaking views. A special shoutout to Andrew, our fantastic host! He was incredibly responsive and welcoming, ensuring that our stay was comfortable and stress-free.

We worked through a bit of calendar scheduling snafu quickly. Scott was accommodating, proactive, and responsive. The condo was in a great location, maintained well, and clean. We very much enjoyed our quick weekend getaway. Thank you!

Was as advertised. Would recommend