Pet-friendly vacation rentals in Olive

We had a great stay at BorisRungcheewan’s place. Check-in was easy, and the hosts sent us all the necessary information well in advance. The only minor challenge was finding the house—it’s set back from the road and located at the top of a long, steep driveway. I can imagine that arriving for the first time in the dark could be a bit tricky. The house itself was just as advertised: very private and quiet. The interior was comfortably furnished, and we especially appreciated the fireplace and the Bluetooth speaker. The two full bathrooms were also nice . The hot tub was easy to use, although a few of the jets didn’t seem to be working. The kitchen was well-stocked with pots, pans, plates, and glasses. The house is about 15 minutes from the Woodstock area and the nearest grocery store, so we’d recommend stopping to pick up any necessary provisions before checking in. Overall, we would absolutely return to BorisRungcheewan’s place for another stay.

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.

The place was super serene and peaceful—perfect for a relaxing getaway. The house was incredibly well maintained, clean, and cozy. Highly recommend to anyone looking for a comfortable and quiet retreat

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 only at Sylvia’s house for one night, but it was a lovely stay. The house was warm and inviting with plenty of space. The loft bedroom was perfect and very comfortable. The shower is fantastic. We would definitely stay here again on another trip to New York.

This is a gem, a peaceful, private place beside a stream behind the big house. The little house is spacious and I sometimes felt inclined to cook during my week long stay, listening to the stream or to music. The bed is very comfortable and there is an air purifier and filtered water. Tuli, the resident dog in the big house is gentle and affectionate. I felt very much at home and hope to stay again.

We enjoyed our stay at Kevin's place. As many others have said, the surroundings are even more beautiful in person. There is another rental unit right across the yard, which we didn't realize, but ultimately we found it nice knowing there were other people around. The kitchen and bathroom(s) were notably gorgeous and comfortable - though we didn't cook, I've never seen a better stocked kitchen in terms of cooking tools at an Airbnb. A spacious and peaceful retreat.

we had a lovely time at Seth’s cottage by the river. Everything was very well appointed and comfortable. I think the beds were the best I’ve had an Airbnb. There was easy access to new Paltz and kingston. I have no hesitation in recommending Seth’s place.

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

The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍

Great place for a quick stop on a trip to visit family. Super communicative and friendly. Would stay again!

Great stay at Jasmine’s well furnished, rustic feel cottage. Peaceful location but just a quick ride to Woodstock, Kingston and Rhinebeck. Pool was perfect - we used it everyday. Heat bathroom floors is a nice touch!

My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.

We had a great time here! It was clean and comfortable, with a perfect location - close to both downtown New Paltz and the Gunks. It was lovely to have tea and coffee in the morning while watching rabbits, birds and deer in the backyard. Our host was responsive and had great suggestions for restaurants and activities. Highly recommend!

Had a great stay! The place was clean, comfortable, and exactly as described. Check-in was smooth, and communication with the host was easy and responsive. The location was convenient and quiet—perfect for a relaxing getaway. Would definitely stay here again!

Ron was quick to respond with any questions we had. The place is spacious and beautiful! The pool was so nice on the sunny days and we even saw a deer walk by when we were in the backyard! Would love to stay here again.

We loved our stay at this beautiful, charming, and peaceful barn. The space was cozy and thoughtfully designed—perfect for a relaxing staycation. The property itself is beautiful, and it’s just a short drive to great hikes, bike trails, restaurants, and breweries. A truly lovely spot to unwind and explore. Thank you for such a wonderful experience!

Great glamping spot. Beautiful location and easy to check-in. Host was very communicative. Wifi speed was decent. The cabin was smaller than some others we've stayed at, if that matters.

Wow, this property is amazing. The light in the church coming through the stain glass windows was so pretty. We took a walk towards the back of the property to see the old graveyard and there was also a pig farm back there. We saw many deer in the morning and at night. Beds were comfortable. Kitchen was well stocked. It was a great place to celebrate my birthday. I’ll definitely be back

Really enjoyed staying at Alan's place. It was the perfect getaway for me, everything at the cabin was very well thought out. Comfortable bed, plenty of firewood, all you really need! Plus - How many Airbnbs have you stayed at that includes AllClad pans and sharp knives? Enough said... One thing to note, there are two other locations on the property for guests - wasn't an issue at all for me, and might even be a bonus for others. Not within sightlines or anything. Alan also has a slick web app you can interface with to get information about your stay, and even get a little breakfast. You could tell significant time was spent organizing and building a good space for guests! I'd definitely stay again!

The Waterfall Casita was beautiful, well equipped, clean and offered lots of privacy. The view to the waterfall was breathtaking. Perfect to relax, connect with nature and get a break from the daily hustle. Would’ve loved to stay longer! We were able to cook meals without any difficulties, the fridge though small was more than plenty of room for the essentials we brought. Jenn was kind, available and communicated quickly without disrupting the peace and privacy. The information about local places and instructions were clear and helpful. Would love to stay again!

A serene riverside retreat offering spectacular views, elevated by the home's impeccable and well-considered design. Thanks Thomas and Carla!

We had a great stay in this peaceful cabin in the mountains. Perfect location central to everywhere that we visited (Woodstock, Hunter, Windham, and the awesome West Kill Brewery). The surrounding area is very quiet and beautiful, and just up the road is a very nice hiking trail. Even though it's a tiny cabin, they make very good use of the space (especially the kitchen where everything is neatly tucked away). I personally loved their coffee station complete with electric kettle, grinder, and french press. Our hosts communicated with us very well, so we had no issues finding the place and getting in.

I absolutely loved this place. Extremely simple and clean, yet has everything you could need. Ana and Peter were communicative and kind hosts. I will stay here again any chance I get!