Cottage holiday rentals in Olive

Highly recommended — especially for families with young children! The property has everything you could need, and there’s even a charming farm nearby (just be sure to check their hours in advance). The hosts were incredibly responsive and helpful throughout our stay. The house was spotless and had such a welcoming, positive energy. With so much land to explore, you truly don’t need to leave the property if you bring your own food and supplies. We had a wonderful experience and will definitely book again in the future!

The perfect stay for horse showing at HITS! My only hesitation in writing this review is that I didn't want anyone else to know about this place for future horse shows! ;) An excellent place to stay with above and beyond amenities, easy check in and great for traveling with a dog. Will absolutely be back!

This was a nice AirBnB for the area, cozy and felt somewhat secluded despite being viewable from the main road. Perfect for a small dog to roam around on the grassy area, and the hot tub looking out into the back was a nice touch and enjoyable to sit in. We were looking for a relatively short get away from the city, quiet and close enough to things in the area to enjoy, and this fit the bill perfectly. The house was very clean with very clear instructions, and nice touches that made it feel cozy. Highly recommend for 2-4 people, particularly with small dogs.

Everything about our stay was perfect! The house was spotless, cozy, and located in a great area. The host went above and beyond — always in touch, helpful, and kind. We truly felt welcomed and taken care of. Would absolutely stay here again!

The apartment was the perfect weekend getaway for my partner and I. We were able to take full advantage of all the great amenities - grill, hot tub, fire pit and a big yard for the pups! The bed and washer/dryer were also a nice plus. Kim was extremely responsive and the perfect host. All in all, we loved our stay and already want to plan our next trip back!

Really a beautiful, peaceful escape. Easy drive to so many adventures! Hot tub while listening to the creek... chef's kiss. Just be prepared for mosquitos, wow. But there was bug spray and citronella candles to help.

Three friends met at this beautiful carriage house with the feel of a French chalet! We stayed two nights with varied weather conditions. The house, grounds and location was perfect. Hot tub was used and so relaxing. The surroundings were beautiful and peaceful. The host, Diane was very helpful and friendly. What host makes scones each morning and delivers them warm?! Visited the Ashokan Reservoir trail, Opus 40, and Woodstock. Recommend this home highly. You won’t be disappointed!

Great place. Fun water activities for the kids. Our dogs allowed to come was excellent. A little light on cutlery in the kitchen, but we made it work. Would recommend and would stay here again!

I booked Nidhi's place for one night for myself and a guest to attend a show at Bearsville. The placement of everything, inside and outside, created an intentional sense of comfort. My guest arrived after me - without a thought, we ended up at the kitchen table talking for hours before the show. Again, the placement of this conversation spot felt intentional, but only after we found ourselves engaged in it. The outdoor surroundings are utilized to not only accent, but to enhance the indoor setting. The whole experience felt private and safe, and allowed us to share a really precious window of time for reconnection and decompression. In addition to the appealing aesthetics (the chosen blue for that kitchen!), the bedding was a treat to come back to at the end of the night - so inviting and equally comforting to find yourself wrapped up in in the morning. Nidhi so kindly messaged me out of concern for the very high winds we were experiencing (prepared with a generator), but no issue.

Such a special little cabin, right by the water. We had a wonderful weekend.

This was our second visit to this charming cottage and it did not disappoint. Amitai is a wonderful host. He reached out after our check-in to make sure all was well, which it was. The cottage is charming, and the surrounding countryside is gorgeous. Our favorite spot at the cottage is the screened in porch that overlooks a small pond. At night there was a chorus of frogs that was sublime. Minnewaska State Park is a short drive away which we loved! There were a few grass cutters and lawn mowers interrupting the quiet which was unfortunate, but when they stopped the peace and quiet returned, and we were happy.

Beautiful home in a fantastic setting, loved every moment of our stay. Really enjoyed watching the deer in the morning while having coffee.

the location was incredible! We enjoyed walking the 50 feet into town for cute shops and boutiques. Ann had a great list in the house of restaurant recommendations that we found very helpful. Pictures do not capture the charm and coziness of this home, it is a very special property. the backyard was gorgeous and large also and we could hear a waterfall in the distance. We loved our little mountain getaway and will definitely stay here when we return to Woodstock.

This was so charming & cozy, while also being conveniently close to nature nails & downtown Woodstock. We thoroughly enjoyed our stay & would recommend!

I had a great stay! My dog and I very much enjoyed the swimming hole and peaceful area

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.

Had a wonderful stay at Michael’s place. Quiet and centrally located to fishing spots we planned to go to. Would highly recommend and hopefully plan a return trip next year.

Awesome stay! Great area, super clean house. Highly recommend!

I had such a great experience staying at this cottage! The photos truly reflect what the space looks like if anything, it’s even more aesthetically pleasing in person. Everything was clean, cozy, and thoughtfully put together. The location is perfect,close to everything you might need. If you’re into hiking, the Ridge to River Trail is just an 11-minute drive away and leads right into the charming and trendy town of New Paltz. We also loved the food recommendations nearby, definitely check out Darlings and Ollies! I would highly recommend staying here. I’ll absolutely be coming back and telling all my friends about it. Thank you for such a wonderful stay!

Great winter retreat. Prior comments referenced a sulfur smell from the water. We didn’t experience that. Great host and dig friendly!

This is our fifth time staying on the property and it is always phenomenal! The accommodations are wonderful, the hosts could not be more outstanding, the surroundings are magical and it is truly a paradise for us! I cannot recommend the Cottage and any other accommodations on this property more! We will definitely be back and are extremely grateful to know about this gem!

We had a short but sweet stay. The surroundings were beautiful and the host’s recommendations were spot on. We highly recommend visiting!

We loved our stay at the cabin and hope to be back soon! It’s was the perfect place for us to stay for our week upstate. We loved the movie collection and listening to the sounds of the creek from the open windows. Really feels like you are at someone’s home and not a soulless rental! Five stars ❤️

My boyfriend and I wanted to spend the weekend away and Teresa’s place was such a beautiful place! The house was four minutes from town super convenient. Teresa gave us lots of recommendations for the wknd which was so helpful! I enjoyed our visit so much I would definitely recommend this place! Thanks :)