Pet-friendly holiday rentals in Middletown

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

Even better than the pictures! This was one of our favorite Airbnb experiences, super cute and eclectic house. We loved the style, the bathrooms made me want to renovate my own, and the beds were too comfortable if that’s possible lol. Perfect for vacation. The house was centrally located to the airport and the Bible museums and printery we booked to tour. Overall, we had just a lovely stay and cannot wait to go back!

We were extremely pleased with Shinto and his house. The house and the surrounding area were more beautiful than the pictures could capture. Shinto was a very accommodating and I couldn’t ask for a better host. Will definitely be returning asap!

This property is large and roomy with plenty beds to go around including the basement with the pool and ping pong tables plus a home gym with various equipments. The outdoors were fantastic with a very nice temperature controlled pool, Jacuzzi, swings set for the little ones and enough acreage to have a soccer match. The neighborhood was nice and quiet in a great country setting with lots of wildlife to enjoy to include lots of singing birds. Our family reunion was a great success due in part to the before mentioned surroundings. Douglas was always available to resolve minor issues, very responsive and accommodating, thanks for making our stay at this property a great one.

Monika's home was one of the best airbnbs we have ever stayed in. The design, style, and quality is something unparalleled in other airbnbs, it has a cohesive, elevated design throughout the entire home. It has everything you could possible need and is so thoughtful in every way. The backyard is huge and is perfect for a family to spend time together. We went on a great hike to a waterfall (which is within walking distance). Location is amazing as it's a close drive to Minnewaska. The location in Kerhonkson is in a nice secluded area. If you're looking for the perfect place to stay in the area this is it!

This was a peaceful, cozy spot to enjoy a long weekend. The river view from both the house as well as the yard was a bonus feature. We spent the evenings enjoying the fire pit by the river and then retired indoors to the large, comfortable living room. Drew was very responsive to our needs of an early check-in which we greatly appreciated. 😊 We would recommend this spot. (Oh, the fishing had easy access, so we we enjoyed that as well.)

Olga's beautiful modern house in Upstate New York is a real gem nestled near a wild forest. The spacious house offers plenty of room to relax and unwind after a day exploring the area. The location offers a perfect blend of tranquility and adventure, with plenty of things to do in the surrounding area. Olga was a fantastic host – incredibly responsive and flexible, which made our stay even more enjoyable. The house itself is stunning, with modern amenities and stylish decor. We had a wonderful stay and highly recommend this Airbnb!

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!

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

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 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!

I had a great time staying here. A lovely and quiet retreat. Douglas and his family were very friendly and responsive to any needs I had. The place was tidy and clean and the grounds around the house were beautiful! Will definitely be back!

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!

Place was absolutely beautiful! Plenty of room and Plenty of space for us to relax. Edwin was very responsive which made our trip go by so smoothly!

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.

Such a charming place - my partner and I had an amazing, peaceful retreat. Felt like the entire place had a lot of thoughtful touches, such as the deck lights on the outside

This was an amazing experience! (If you’re using Apple Maps, go to the right off of Minisink, not left! ) no complaints, just a heads up the internet connection isn’t the most stable so if that’s something you need, maybe have a hot spot. The house is well kept and comfortable, extremely peaceful. Marcus replied quickly and was very helpful

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 appreciated the cleanliness of the house, and it was a nice place to relax with friends and family both inside and outside around the fire. We would definitely stay again!

Second time staying here. Looking forward to a third stay next spring. Excellent communication and clean, comfortable house.

Such an awesome spot! BUT note this is a glampsite rather than a full house. The toilet is an outhouse (very clean, but make sure to duck to not hit your head), the shower is heated but it's outdoor, I didn't have soap or towels provided that I saw, and the bed is a tri-fold mattress that folds out onto the floor of the little A-frame. The wood fire hot tub was amazing, the fire pit is nice, there are two chairs included, parking is easy, there is good quality firewood here but bring something to light it with and start the burn. The sound of the running water is worth every penny. The cabin also is heated via some sort of gas, which does a great job and making the space feel cozy but I woke up with a pretty good sore throat. Not sure if that is a coincidence or if from the heater. Overall, I would HIGHLY recommend this place! Just make sure the less earthy people in your group are not expecting a hotel room/house.

We had a wonderful stay. The home is comfortable and decorated thoughtfully. It was a pleasure to enjoy the views of the river and to take in the natural setting.

Hikers Haven is a great place to stay for a weekend. The place has a cool, tidy vibe. It is peaceful and close to both nature and towns. I highly recommend a visit to the Bashakill if you stay here.