Pet-friendly holiday rentals in Olive

Donna's place was amazing! We knew we would love it from the pictures but were even more blown away when we walked inside. It was the perfect cabin with every amenity and more that you could want for a remote get away in the Catskills. We went up with our dog and loved every minute - will definitely go back for our next trip up!

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

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.

What an excellent stay - this airbnb was incredibly well stocked with kitchen supplies, games, extra linens, really anything that one could want. Amenities were high quality and very thoughtful.

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!

Substantial and comfortable space. Very well appointed property with hot tub, bath and kitchen with clothes washing facility. Great views and well located near some lovely towns. We had a big car and parking was slightly tight to turn but a very minor observation!

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.

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!

The teahouse and surroundings were relaxing and peaceful. We saw groundhogs, deer, and chipmunks from the porch and our 2 dogs loved exploring the field and wandering in the nearby woods. The pool was amazing and warm despite the rain and the natural landscaping couldn’t have been more beautiful. We really enjoyed our stay!

Karali is so great about recommendations and ensuring guests have a lovely experience!

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.

Absolute slice of heaven. Private, peaceful. Home itself modern and comfortable. Pool was absolutely amazing, comfortable in late May - in peak summer it must be amazing. Would love to stay again!

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

Another absolutely perfect stay at the farm!

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

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!

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!

The room was comfortable and clean, we enjoyed our stay and would stay again!

Beautiful modern A-frame cabin tucked away in the woods. Amazing attention to detail on the inside & out. Easy drive to some great hikes & restaurants. We didn’t want to leave!

Alexandra’s cabin is the peaceful, private retreat that dreams are made of. We’d never actually stayed in a tiny house before, but the thoughtful design ensured it was perfectly comfortable for two people and our pup (the stairs to the sleeping loft are steep, so might be tough with any mobility issues; our pup slept downstairs in his bed). The WiFi is more than sufficient for taking video calls and working remotely, and the air conditioning ensures you can stay cool if you have to stay inside on a hot day. This is one of the few Airbnbs we’ve stayed at where all outdoor amenities are actually available as described - we grilled out every night (purchased charcoal and lighter fluid at Tops in Tannersville, used the provided chimney to start the grill) and drank cider around the firepit (tons of dry wood provided, pit was dry and ready to go, gathered kindling from the property, brought our own fire starters) while the sun set over the mountain. Perfection.

Loved it! The cabin is perfect. And quiet and nestled in the woods. Great for dogs too. And there’s a wonderful hike up Mt Gaurdian right at the theatre. A nice retreat from the city right in the heart of Woodstock