Pet-friendly holiday rentals in Callicoon

This place is an absolute gem. From the moment I arrived, I felt a deep sense of peace—it’s incredibly tranquil, surrounded by beautiful natural scenery, with a running stream just steps from the front door. The home itself strikes the perfect balance between rustic charm and modern comfort. Inside, the decor is thoughtful and unique: a nostalgic mix of vintage childhood sports photos, striking modern art, and beautiful antiques. It all blends together to create a space that feels both stylish and deeply personal. The fireplace is a centerpiece—warm, inviting, and stocked with enough firewood to last all summer. This isn’t just a house—it’s a welcoming home. You can feel the care and intention behind every detail. Located just 15 minutes from Bethel Woods, it’s the ideal escape from NYC. I can’t wait to return.

First Stavros was a stellar host. Proactive in communication and always responsive. Very attentive, we had one small interruption with the wifi that he promptly addressed before we even noticed! The house property is absolutely stunning and gorgeous, peaceful, spacious, very beautiful. The house has everything well stocked. Kitchen had plenty. I can't find one thing to comment that isn't positive. We all enjoyed ourselves to the max. The most enjoyable was the three walls full of windows that made the thunderstorms so beautiful to watch in the living room. The little stream in the back so pleasant to sit silently. An incredible house and even more kind, generous and helpful host

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

Jordan’s home was breathtaking. The views were spectacular and the neighborhood was quiet. The home was nice and clean and was enough space for me and my friends. Jordan was great to communicate with and left clear instructions for us for check-out. She gave local recommendations and I am thankful she did as Jensen’s Ledges was out of this world. I would definitely stay here again in the future. It was worth every penny and more!

No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

A wonderful retreat for either solo or a couple’s weekend. I felt right at home. If you’re looking to have a movie night during your stay I suggest downloading content prior to arrival. Internet service is available but it’s a bit slow. Otherwise enjoy this quiet, reflective and cozy space. It’s worth it!!

Very good and clean place for relaxing and enjoying the nature, thanks Vanessa.

Great place to stay after seeing a show at Bethel Woods. Easy to find and less than 15min drive to catch the show. Erik was easy to work with as well. We will def book his place again when we come back for another show!

This A-frame escape was exactly what I needed — the perfect break from the city. The place is beautifully designed, cozy, and filled with thoughtful touches. The jacuzzi was absolutely incredible, especially under the stars at night, and the A-frame structure made the whole stay feel like a peaceful retreat.

The Hideout was such an amazing place to stay and the A Frame was exactly what we were hoping for. It had everything we needed and Samantha was very communicative the whole time. A perfect weekend with the toddler and the dog!

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

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.

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!

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!

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!

We loved this Airbnb. It was beautiful there and Michael was quick to answer any questions. We did manage to get on the water with the kayaks, so that was great. We will definitely be back.

We had a wonderful time at Eric's place. If fit our family of four and our two little dogs perfectly. We went to Bethel, NY to see a concert at teh Bethel Woods Center for the Arts. It was only a 20 min. drive. The people in town and nearby towns were very friendly. I highly recomend Eric's place. I don't think you can find a better place to stay in the area.

It was a wonderful stay in such a cute town! We really appreciated the fact that it was pet friendly! My boyfriend especially loved the shampoo and conditioner that was in the shower- he said it smelled incredible. Also, the bed was incredibly comfortable. The power ended up going out (while we were at the wedding reception!) and Susanne was proactive and reached out to make sure we were okay and had everything we needed. We will definitely be back and would love to stay again when the time comes!

What a wonderful experience from beginning to end. Roy and Axels house was amazing. And from the very beginning Roy was amazing looking after me and my girlfriends. (We went up for a wedding) Such a lovely town and the people are so friendly. The food is amazing. Clearly this is where all the great Chefs are hiding. Roy suggested a couple of places and he was on point. I just can’t say enough about Roy, Axel, the lovely home and this quaint little town in the Catskills.💐

We had a great writing retreat here! Hopefully we'll be back at some point.

Lovely, gracious, beautifully-decorated house. There's plenty of space -- it's bigger than the pictures make it look -- and everything was very comfortable. Leah was extremely responsive and made sure we were happy. - In a rainy May, it's less "trails" and more "trackless woodland" - You'll want to bring your own matches and containers for leftover food, but there are plenty of plates etc. for a big group. - I was worried that the road would be disruptive, but it still feels very secluded; aside from a few trucks Monday morning, I barely noticed it. We had a great time, and the area is beautiful!

Stayed 3 days with my husband, 2 teens and dog. We had a fabulous stay! I can’t say enough good things about this rental. Private & secluded but close to town. Extremely clean, comfortable beds. Lots of space for our dog to run. We enjoyed beautiful views with a rainbow one day and loved the fire pit. We’ve stayed in many Airbnb rentals and this might very well be our favorite one. Thanks Kirk for a great weekend.

The Blue Caboose is a great house—extremely comfortable and overall a wonderful place to relax. We got there on a Wednesday and did not leave the property at all during our three-day stay. There is space to walk around outside, with lots of trees, and a path down to the lake. It’s quiet and I found it an excellent and serene place. Great screened-in porch, too!

Joseph's home right outside of Bethel was the perfect place to stay for a concert at the venue! It was peaceful and close enough to the venue and other sweet little towns. His home is pristine! So much thought went into the decor. The beds were OUT OF THIS WORLD - with bedding the quality of a five star hotel. The patio was serene and private. It was a DREAM!