Pet-friendly holiday 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!

My boyfriend and I were looking for a relaxing weekend escape from NYC and couldn’t have picked a better spot. We came to explore Kingston but loved the house so much that we were just as happy staying in, playing games, and soaking in the cozy vibes. The home is beautiful and thoughtfully appointed — I can only imagine how magical it must be in the summer with the porch, or in the fall with the foliage. Even in late winter, it was idyllic. The location is perfect — just about 10 minutes from Kingston, so it’s super easy to pop into town while still feeling tucked away. We’d absolutely stay here again!

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.

We had such a lovely weekend staying in this cozy cabin. The views of the river and ridge from the yard were beautiful and calming. We were able to have a late check out with ease! Definitely will be back to stay again!

A very lovely place to stay! The description matched the place exactly. We enjoyed spending a lot of time outside on the deck bird watching and even saw some fish jumping in the river. The property is also very private which was a huge plus -- no visible neighbors in any direction while spending time outside. Seth was a very responsive host and did a great job with the design of the house. There were lots of thoughtful touches that made the stay extra nice. Would love to stay again!

I couldn't believe how responsive Agnieszka was! She made every effort to make sure my husband and I had a great stay. Her comfy deck, cozy fireplace, and nice shower were a godsend after my husband and I decided to brave a rainy hike. I think the place is very reasonably priced considering access to a pool and laundry are included. It's just down the street from hikes and resturants. I also enjoyed taking classes at Mountain Breeze Yoga just down the road.

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

We enjoyed our stay here very much. Richard was extremely responsive and made everything so easy for us. He even recommended the amazing Ice Caves for our hike and it did not disappoint! Even though it rained a lot, we were still able to get use out of the hot tub and the pool on our last day. The water is soooo stinky though (as advertised) - a little hard to get used to but indeed great for your skin and hair.

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.

I do periodic weekend trips upstate and this barn immediately earned a spot on my list of saved accommodations — the space itself is so cozy, the immediate surroundings are picturesque, and it’s just a short drive to a bunch of great trailheads. Ideal spot for non-camping outdoor enthusiasts.

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!

We really enjoyed our stay! It’s close to hiking, restaurants and downtown Woodstock. The home is very unique, with a mix of modern and rustic decor. Very spacious, comfortable and clean! The full glass walls overlooking the river in the backyard is just stunning. So beautiful and peaceful no matter what the weather is during your stay. I would highly recommend this place!

Beautiful and peaceful place in the Catskills. Located on a private road that is easy to find, and easy to walk around with your pups. LeAnna is a great host. She is easy to communicate with, and provided great local recommendations. I recommend bringing some snacks and fruit as the closest grocery store is a little sparse.

This place is as incredible as it seems in pictures. The space is very well thought out and built. It’s secluded with a lot of space to spread out. The bathhouse is everything!

Jeff and Sharon were wonderful hosts and the airbnb exceeded our expectations. It was clean, nice, and had great amenities. The creek in the back was beautiful. Jeff and Sharon were also available and responsive the entire stay. We couldn’t speak highly enough of this airbnb.

When I decided in February to take three weeks away from my home city to spend time in the mountains, I wasn't sure I'd come a place that ticked all the boxes: would let me bring my dog, was on top of hiking by not terrifically far from essential businesses, was within a 4-5 hour drive from home, had the comforts I knew I needed and-- would also let me bring my cat? What did I find? This total gem of a cabin. My animals and I were able to make ourselves comfortable, the views of the lush trees were instantly calming, the bed was super comfortable, and somehow even though it felt like the middle of no where, was a 30 min drive from so many beautiful villages, trailheads, and other Catskills goodness. Mark was super on top of communications, helped me out when I needed it, and made sure I had what we needed. Highly recommend a stay here-- can't beat the charm and being truly surrounded by stunning nature.

My husband and I arrived late, around 9:30pm, because we had commuted after work in NYC. Everything was impeccable. The home is perfect in some many ways. We felt very comfortable and got an amazing night's sleep. The following more we had to head out early to pick our daughter up from Binghamton. She stayed with us on our second night. Nicolette's and Tim's Tiny Horse Barn is so perfect. It is exact amount of space we needed. Even though the space is space, there were 5 tissue boxes in perfect locations. This may seem a small thing to some. But if you have allergies, it is SO appreciated. The kitchen was equipped with keurig coffee pods, creamers, sugar, tea kettle and more than everything we needed. Equally the bathroom was perfect. The beds were super comfortable as was the temperature. There were plenty of great restaurants nearby. The attention to detail is amazing. Everywhere there are little hints of horses, but not in an overwhelming way. We actually are having book sent :)