Pet-friendly vacation rentals in Middletown

Having a current child / Cadet at West Point and also another child / graduate of West Point , we always make it a point to stay at different Airbnbs in small towns around the USMA on both sides of the Hudson River . Melanie ‘s place was wonderful. Plenty of rooms/ beds for our Parent Weekend visit. Peaceful and safe location , yet a short 20 minute drive to the Academy . We felt right at home and look forward to staying at Melanie’s place again . The house was very clean and we had no issues at all !! Thank you

Beautiful place and stay! Private, cozy & peaceful, yet close enough to fun places like Hudson and Kingston. Martina was a wonderful host, super responsive with tons of great recommendations. We absolutely loved our stay!

The place was well stocked and clean upon arrival. We had a bit of trouble with the lock at first, but then everything got sorted, Leah was quick to respond and check in with us to make sure everything was going well! The area is quiet and about a 20-30 minute drive away from most things. There was a lot of open communal space for our group to hang out. Kitchen and bathrooms were perfect.

Ruth’s place was perfect for our short getaway to take the kids to learn to ski. Plenty of space and clean. Easy to get to. Would come back next year for some more ski lessons!

I have been to many places but this house was top notch I'm glad I got to stay there with my family. everyone was very happy with the property. I would like to stay in the summer as well

PURE BLISS! The cottage is old, charming, and sits in a beautiful location with amazing views and access to the Delaware. So many varieties of birds to watch. The indoors is very clean, beds comfy, kitchen adequately supplied to cook any meal (but go to TOWN!) Beautiful place to have campfire and relax. The outdoor space is beautifully laid out. The neighborhood is absolutely lovely to walk and the downtown is worth exploring. Hosts were very quick to respond to my texts. The fresh eggs left in the refrigerator were a plus. I can only imagine how awesome this place will be in the summer! Thank you so much! See you again, for a longer stay.

We were looking for a place to unwind and we did with Seth’s place. Right on the river, great views, enjoyed the hot tub and very comfortable beds! We had a relaxing time.

We spent the weekend at this amazing farmhouse and didn’t want to leave—seriously, we were this close to moving in. Mark and Whitney were absolute gems of hosts, making us feel instantly at home with everything we could possibly need. The vibe? Retro charm meets cozy comfort. The kitchen counter was so long and inviting, it became my hangout spot whether we were cooking or just chatting. My daughter claimed the little lounge outside the second bedroom as her study nook, our family friend took over the artsy fashion studio room, and my wife fell in love with the living room—aka the evening chill zone. We shared family-style dinners in the dreamy dining area, melted into the comfiest beds ever, and just when we thought it couldn’t get better… enter the old-school record player. Dropping the needle on vinyl while we lounged around? Pure, unexpected magic. The whole place had this nostalgic, feel-good energy that made the weekend unforgettable.

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.

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!

Lovely quiet, pet-friendly place above the garage but note that there is a steep staircase to get up to the second floor. Very friendly hosts - greeted me on arrival and had left the door unlocked so entry was easy and the key was available for my use. Comfy bed, cozy and warm rooms with remote-controlled mini-splits in both the living room and bedroom. Bathroom with tub and separate shower - the water pressure was not as strong in the shower as I would have liked, but it was nice to have the skylight in there. My GPS found it easily but a larger sign with the house number would be helpful, especially at night. I would definitely stay there again.

Beautiful home with amazing views. The house was very clean and spacious, the views were amazing. Susanna was very responsive and gave clear instructions. We had a very relaxing weekend and enjoyed very much staying at the house. We would love to come back.

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.

My wife and I stayed at Ron’s place for five nights for a winter getaway. We had a great stay, highlights include a comfortable king bed, a quiet setting, a cozy fireplace, and the large ground floor bathroom that feels like your own spa- we thoroughly enjoyed the sauna, huge bathtub, and rain shower. Ron was a great host and was very responsive with any questions we had. We spent many hours watching TV on the screen and projector set up, we grabbed more pillows from upstairs to add some more cushion to the leather couch downstairs.

Excellent stay for a small group - we only stayed for a weekend, but would be a perfect spot for a weeklong trip as well.

This was such a nice space and Lisa was a nice and accommodating host. This place is full character and wonder. Very artistic color energy in this place. We started my daughter’s 18th birthday celebration here with what is her last sleepover with friends. The hot tub, steam room and sauna were the first things and last things used. They enjoyed it so much! Thanks for your hospitality Lisa. If we ever need something like this again. We will be sure to look you up! Blessings

Jonathan’s stay was amazing! Super peaceful sweet spot! Place was exactly like pictured! Cleanliness was an A+ for me! Cozy atmosphere. Fire pit area was nice as well! Host was super accommodating which was great, Super responsive!

Incredible home! We spent the weekend here with our dog. The large fenced yard was amazing for her. The house is tastefully furnished and very comfortable. The view is wonderful. The town is less than a 5-min drive, with wonderful cafes, restaurants, a grocery store and some cool shops. Great place all around and a good size for a larger family or small group of friends too. Thanks for a great weekend!

A gem in the Pocono mountains! Skippers place is perfect for a small group of travelers (and dogs!). It’s quiet, peaceful, and comfortable. There were plenty of fresh towels, seating spaces, and a fully stocked kitchen that was ready to go for our meals. However, if we wanted to go to town to eat, Skipper provided plenty of recommendations. The hot tub & wood burning fireplace was perfect for our long winter weekend getaway. The home is pristinely clean, washer & dryer available, dishwasher, and giant refrigerator. We couldn’t have selected a better option for our group! The beds were also extremely comfortable and perfect for us. Thank you very much for your hospitality! PS: Skipper is a great host and worked out an early arrival for us too!

My husband and I had a great weekend celebrating our anniversary. The house was very clean and was just as described. The hot tub was great. Yard was private and relaxing. Just what we needed. Close to Bushkill falls which was beautiful.

We had a brief stay, but what a cute place. Bravo! Was perfect place for us!

Orna was so welcoming and easy to communicate with. The apartment is cozy and well appointed. We were visiting our daughter and family for Thanksgiving. They recently moved to Kingston . Great location! This would not affect most people, but my 90 year “young” dad was with us, so the old fashioned tub/shower was a bit of a hazard for him. Really a gem of a place if you are traveling through or visiting loved ones in Kingston.

Wonderful house in a very nice place! The accommodation is very clean and fully corresponds to the description! The owner is friendly and very attentive to his guests! Will definitely come back!

Maria and Max’s place was everything we dreamed of! It was a nice seclude, a cabin with a large backyard and a wonderful fire pit. We loved the decor inside the house, the beds were extremely comfortable, and everything was as described. It’s in a great location approximately 20 to 30 minute drive to multiple cute small towns in Catskills. We can’t wait to bring our friends back next time!