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!

We had a lovely stay at kim’s. The location was great, having a hot tub was really nice even with the weather getting warmer, the space was very clean and kim was very responsive to us throughout the whole stay.

Couldn't have been happier with this cottage. Modern appliances, beautiful surroundings, quiet, gorgeous view overlooking the lake. The kitchen and master bathroom were standouts. Would stay here again. Bob and Julie did a fantastic job communicating before, during, and after the stay.

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!

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!

This cabin is so very special—and has an artists touch! It is cozy (especially with the wood stove going), spacious for being a one-room size, and has everything you need to disconnect and recharge. We will absolutely be back and appreciated the clear and easy communication as well!

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

Very well located and cozy spot, great fire pit and backyard area! Nice for a cozy get away.

It was an incredible experience. My family, my two dogs, and I thoroughly enjoyed our stay. Upon arrival, we were greeted by our wonderful and attentive host, John, who helped us carry our bags and belongings to the cabin. The house is a cozy 1930s cottage, nestled on a hill in a green meadow, offering peaceful views in a pristine and tranquil setting overlooking the Delaware River which was directly in front of the house. The house features beautiful antique furniture, a well-equipped kitchen, and comfortable beds. We especially liked that the house was dog-friendly. It was a haven for them! It was amazing to see marmots, deer, eagles, and birds of various species, which were all part of our enjoyment. We will definitely consider staying here again and highly recommend this place to anyone looking to relax and be in touch with nature. Thanks again for allow us to stay in this wonderful Place, John!

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 :)

Rick’s place is great, a nice porch area and two comfortable bedrooms, and the AC is powerful for hot summer evenings. Rick was an excellent communicative host who was at the ready to help out with any issues we had. The only thing, and perhaps I misread something, but I thought it would be more secluded, the 130 acres threw me off. Still, it’s very private and I would recommend this place for your visit to Rhinebeck etc.

We had a wonderful stay at The Carriage House and would definitely book it again. It felt like a true escape from city life. Very cozy and comfortable and had everything we needed. The house was perfectly located near High Falls, Accord and Stone Ridge so we got to eat at great places and explore each of the towns without needing to spend much time in the car. Would recommend this place for anyone looking to spend some time in that area. It was truly a lovely experience.

Easily one of the nicest little cabins around. Can’t beat the privacy / grounds with Mountain View’s. There are nicely landscaped walkways and paths all around. We also appreciated the convenience of firewood and drinks for purchase on the property. Great location for hiking, snowboarding, fishing, not far from breweries like west kill, and towns like Woodstock. Paul was a great host who was very responsive to any questions we had. Will definitely book again.

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!

We enjoyed our stay in this house. It is quaint and peaceful. Marc is a great host. The view in the backyard is nice and has a perfect spot to sit and relax. The house is small but accommodates two people nicely.

Jaclyn's airbnb is located in a wonderfully private area in the Catskills, close to New Paltz and many nice restaurants, amenities and hikes. The small home has been tastefully remodeled and outfitted with great appliances. A perfect getaway for a couple. We will be back!

Lovely stay! Cottage was very cozy and Monica was very responsive & helpful. Would have loved to stay longer to fully enjoy what the cottage & surrounding area has to offer.

We loved it we had such a great time with our two kids. A good getaway away from New York .Beautiful views cozy home and we heard the birds chirping in the mornings. We will definitely be back thank you so much for.

This whimsical cottage was a dream of a lodging. It was cozy and clean, and there was a manual left to help us navigate the towns close by the walking trails and the water features behind the cottage were absolutely incredible. This Airbnb was worth every penny.

This was our second stay at this home. We have come to expect only the best from this host and we’re not disappointed!!