Family-friendly vacation rentals in Middletown

My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.

Peaceful surroundings, beautiful lake, wonderful house and amazing hosts! Had an absolute ball kayaking, fishing, and enjoying nature. This was my second trip and can’t wait to go back again.

I've been to the Appalachian a few times over the years...this unit was clean, updated and spot on...near the elevator and great view of both the pool area and the mountain.

Gorgeous house, super clean and tidy inside, with comfy and modern furniture. The hot tub was fantastic, make sure you turn off the lights so you can see the stars! The only other heads up I’ll give is that the way to get in is through the back entrance! We tried the front door for like 5 minutes until the electronic lock blocked us from continuing haha. Great location to get away from the city for a weekend and go hiking. Lots of great trails really close by.

Our whole family loved our stay at the very cozy and tastefully decorated Roscoe Retreat. The property is well taken care of, has everything you could possibly need and we felt right at home. A perfect escape to the country and we wouldn’t hesitate to return in the future! Thanks again.

Julie's place was the perfect winter getaway. The fireplace, hot tub and sauna warmed us and the very well-equipped kitchen enabled us to prepare great meals. The house was beautiful, with two living rooms for different activities and energy levels, a game room downstairs, a dining room with a large table and chairs, and comfortable furniture and beds throughout. Julie texted me to make sure that our every need was met. We had a snow and ice storm, and she had the driveway and walkways plowed, shoveled and sanded twice, and kept plenty of salt on-hand. We hope to return sometime in warmer weather so we can enjoy the pond, too.

We had a nice time staying. It has a Well stocked kitchen. It is near to grocery and shopping in Stone Ridge. It has Great fireflies at night and a good view of the sunset.

Choosing to stay in Porter's container cabin was the best decision we could have made for our vacation. It was so peaceful and relaxing. We had daily visits from a beautiful deer, and countless butterflies. We chose to use this time to unplug, and really connect with each other, and we could not have chosen a better place to spend our time. We've missed the view from the front door every day since we've left, and we're already planning to come back next year. Thank you so much for having us.

Spent a week in a cozy cabin tucked away in the woods, and it was exactly the reset I needed. Peaceful, quiet, and surrounded by nature—waking up to the sound of birds and falling asleep under the stars felt like a dream. The cabin itself was warm, clean, and had all the essentials. Whether we were sitting by the fire, going on nearby hikes, or just enjoying the view on the porch, every moment felt grounding. No traffic, no stress—just stillness. Highly recommend if you’re looking to disconnect and recharge. Can’t wait to go back.

We loved the place, it was a beautiful home with lots of light and accessible green space. It was perfect for a short getaway. It’s a short drive from nearby towns and was very easy to find based on the directions. Mark was a responsive and accommodating host and we had a wonderful time in his airbnb.

Peaceful and private! Situated on a dead end lane Patrick’s place had plenty to do outside - exploring the stream, near by waterfalls, local parks and attractions. Lake Superior State park and the Toronto Reservoir were great spots for swimming and exploring. The house itself was clean, comfortable and well stocked with all necessities. The yard provided a great space for pets and kids to play in addition to exploring the various seating areas and fire pits on the property. There were also many wildlife visitors from deer to fox. We will definitely consider staying 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.

Jessica's restored barn is amazing and one of the best Airbnb experiences we've ever had! The photos don't do it justice! The barn is unique and has the most incredible views! The sunset experience is A++, and the deck is the most serene place to have your morning coffee. The most impressive part is how clean the space is- I'm not sure how she does it! The kitchen is stocked with everything you need from a popcorn maker to a vitamix. There are spaces to sit, relax and nap in every corner of the house. It is immaculate, thoughtful, peaceful and comfortable. Bonus- if you love music, there is an insanely good CD & record collection. Jessica was so responsive to any of our outreach and we will 100% be back. *10/10 would recommend, this place is a total find!!

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 had a wonderful weekend trip at Tony’s lakeside cabin to celebrate our anniversary. The setting was idyllic, and the cabin was cozy and comfortable. We loved waking up to the beautiful view of the lake! Tony was a friendly and helpful host, and the whole weekend went very smoothly, from check in to check out. We would definitely come back!

Yi's Place is a cute cottage style with tons of old charm, the view is breathtaking and exquisite. You need to really like vintage retro home style and appreciate nature to appreciate the stay. The host is very thoughtful and provides everything needed for the stay.

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!

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.

We loved this place and would recommend to everyone! Jennifer and Jose were so kind and communicative and so helpful! It was such a beautiful place and we would definitely book again! Thank you for everything!!!

We had a wonderful stay at this house. It was clean, spacious, very warm despite the cold, and had a terrific pool table and air hockey table. Our family relaxed and spent good time together.

We had such a great stay at Eugene’s place! The house was perfect for our group — spacious, comfortable, and full of fun things to do. We especially loved the private theatre, the hot tub, and especially the sauna — such a great touch! The volleyball net was a hit, and there were tons of games in the closet that kept us entertained. The kitchen was well-stocked and roomy enough for us to cook meals for our large group, and there were plenty of different areas to hang out in, everyone could find their own space to relax. The towels were plentiful (huge plus) and having access to the washer and dryer came in handy during our stay. Eugene was a fantastic host — super friendly, very responsive, and just really helpful all around. We also got to enjoy a few deer sightings right in the yard, which felt magical. We visited the nearby alpaca farm and did the Beer Mountain hike, which was a nice outing. All in all, a wonderful stay. Would absolutely come back. Thank you Eugene!

Perfect location — it’s directly in the middle of Minnewaska State Park and downtown New Paltz. Stargazing in the hot tub was a perfect way to relax after a long hike.

Three friends met at this beautiful carriage house with the feel of a French chalet! We stayed two nights with varied weather conditions. The house, grounds and location was perfect. Hot tub was used and so relaxing. The surroundings were beautiful and peaceful. The host, Diane was very helpful and friendly. What host makes scones each morning and delivers them warm?! Visited the Ashokan Reservoir trail, Opus 40, and Woodstock. Recommend this home highly. You won’t be disappointed!

We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼