Pet-friendly vacation rentals in Callicoon

Brett is the best. Supportive, communicative and very helpful. We highly recommend!

We’ve stayed at Skip’s listings a few times, and it’s been wonderful each stay. Skip is helpful and quick to answer any questions. Andes is the most beautiful town. Highly recommend!

We spent a wonderful, snow-filled weekend in the woods at this property and loved every minute of it. This home is spacious, homey, and secluded in a beautiful corner of the Catskills. Fantastic for kids and dogs, as advertised. We would absolutely return!

Lovely weekend get away from NYC. Beautiful home with lovely decor. The bedrooms were cozy and with comfy beds. Wonderful deck to enjoy the beautiful view and the backyard was great, our dog enjoyed running around.

Absolutely loved our stay! We were looking for quiet, peaceful, and lots of R&R. Bruce was easy to get a hold of and very helpful. Highly recommended!!!

This was a perfect house that felt like home for my family and I. From checking in to checking out and everything in between, Kasey was kind, accommodating, and highly responsive. She went above and beyond to make sure we had the best stay. She and her home made it very easy to feel comfortable. I loved the simplicity of her home, the minimalist approach so we didn’t have to worry about all the “things,” and the warm feel overall. From someone who has stayed in my rentals, this has exceeded my expectations. Thank you so much!

This house was great! We stayed 2 nights. Very nice, useful kitchen 100% , can be found anything needed for cooking. 2 kind of coffee maker machines, 5 different ground coffee are in the refrigerator, ready to be made. The whole house was spotless. Laundry located in the basement with laundry detergent and softener on the shelf. Too many great things to mention! I would recommend to family, friends and anyone looking to stay in the area!

A quiet and private area. A neighbor on one side but never heard or seen anybody. Plenty of room for the dogs to run and hiking trails across the street. It is well stocked but does need some updating.

Our group had a great time at Anna’s place. Spacious and comfortable with great views. Anna is very responsive and gave clear check in instructions. Little communication needed given her detailed instructions, and the little communication needed- she was very responsive.

Our family loved staying at Elyse's home! The big kids had a blast playing the games in the basement while the grown-ups enjoyed cooking in the well stocked kitchen. The home is beautifully decorated and comfortable. Elyse went out of her way to ensure the driveway and walkways were salted as there was a lot of ice. She was a wonderful host and we would definitely return!

Nice little getaway during the cold season. The hot tub was excellent and about 100 degrees so perfect even with the cold temperature. It was still possible to put together a meal with the propane grill and warm things up in the microwave or store them away in the fridge. The heat was excellent in the space. Seems like it would be a great place to stay in the summer as well!

Great place. loved the pool table, darts and shall shuffleboard. lots of good wineries and cider places within 25 mins. pennings is our fav. didn't use the hot tub so couldn't comment but looked nice and private. driveway is steep but easily driveable. recommended. also didn't have coffee filters and they paid for some to be delivered same day! sweet.

Our stay was very relaxing and we enjoyed it thoroughly. We appreciated the attention to detail in the amenities and the thoughtful touches that included our dog. It was very clean and the kitchen was fully stocked with everything we needed. The setting is beautiful! I loved having my morning coffee watching the lake. The little lake house was perfect for a weekend getaway. We wish we could have stayed longer and hope to return soon! We 100% recommend it.

Came up with some extended family and a pup for a long weekend. House was bright and clean and we loved the surrounding property. Hot tub was great as the temps dipped while we were there. house had a lot of original charm with many modern touches.

Great spot for exploring with dogs! The neighborhood includes another house that I believe John shares with family and friends, so we weren’t entirely alone in the area—which I personally found reassuring. If you’re looking for complete seclusion, it’s a good idea to confirm this detail with John. Right behind his home, there’s a trail perfect for morning strolls, and the location is very accessible for road cycling, which I thoroughly enjoyed. It would also be a fantastic base for mountain or gravel biking adventures! John’s place was spotless, comfortable, and had a nice bathroom with plenty of hot water. Highly recommend!

Great Airbnb, from the moment I booked to the morning I checked out. Communication was friendly and prompt. There were no surprises at all - good or bad, everything that were expected and seen from the Airbnb post was delivered, and well delivered. A very charming home with plenty activities to do inside - full game room and open concept kitchen where we spent half of our time ( It’d be nice to have the TV above the fireplace so whoever is cooking can be part of the entertainment as well) My favorite room of the house, “The Sunroom” An early bird myself, I spent all my mornings there, as coffee was brewing, I would fire up the wood burning fireplace. While most of our party were still asleep, some of us would drink coffee while staring at the fire and watching the sun rise through the glass wall. Simply rejuvenating. Summarizing, everything you see online you’ll find at the house , can’t go wrong! Book and Enjoy!

We had a wonderful time at Nick’s Place. Great wood cabin with very warm heating during our stay where we had a snowstorm. Very cozy and wonderful view of the mountains.

Place was amazing! Views from the place were fantastic and the drive to Elk mountain was just short of 20 minutes.

Awesome place! Very peaceful, secluded, and plenty of room for our group of 6. We enjoyed the front deck that offers a great spot to enjoy the fresh air and get some nice views of the surrounding area. The kitchen was spacious and had everything we needed and more. Not necessarily a complaint, but understand there is either a $500 refundable deposit or a $70 non-refundable charge for the booking. This is not common in my experience on AirBnb, but is required for the booking, so just wanted to put that out there. Overall, this is still 5 out of 5 stars for many reasons and I would highly recommend staying here.

beautiful little place in the middle of a quiet neighborhood, just a few minutes from Greenwood Lake and Warwick. Julie was super responsive and very helpful! One thing to note - though the listing says up to seven people, it would definitely be a squeeze. me and my boyfriend stayed there with a friend and that was the perfect amount of people.

Jeff and Sharon were very responsive and provided us with everything we need to have a great time!

Great place to stay. It was very clean and the bed was so comfortable I felt like I slept on a cloud. The rooms feel huge for such a small space and the bedrooms are far apart so it’s private if you’re sharing with friends.

Really cute place. Comfortable beds and Sofas. The propane fire place was ideal. It was cold and icy when we stayed and we pretty much stayed in the whole time. It felt very warm and cozy. John was very responsive and helpful, he made the whole experience very easy for us.

My husband and I spent our wedding night and the first part of our honeymoon at Julius’s tiny home, and we could NOT have made a better decision! It was such a beautiful and peaceful experience. It is close many local restaurants and places that we hold dear such as “Heaven’s Embrace” by Eternal Flame of Hope Ministires. The direct river assess provided breathtaking views both day and night, and my husband even caught a glimpse of a bald eagle catching a fish! The home itself was adorable and just the right size for the two of us! We loved spending time outside by the fire while listening to the river. Julius was so very kind and informative throughout our entire experience! We truly can not recommend his tiny home enough, or any of his other properties which I hear are just as beautiful as well! The only “issue” that I believe has been noted before is that the water smells at times; however, it wasn’t a huge problem for us, and would definitely NOT stop us from booking again! ?