Photo by Vincent Ramundo

Middletown house rentals

We found 1,946 house rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday home rentals in Middletown?
Opt for one of our 1,946 holiday home rentals in Middletown and you'll have a perfect base for your next great adventure. Mechanicstown, Washington Heights and Howells are among the city's best areas to stay.
How much does it cost to stay in a holiday rental house in Middletown?
Discover a variety of holiday home rentals in Middletown, where prices vary to suit every preference. From affordable choices to high-end properties, Stayz makes it simple to compare options and narrow your search to find the best stay for your getaway.
When is the best time to rent a holiday house in Middletown?
Most Stayz guests prefer to stay in a holiday home rental in Middletown during August. At this time of year, the temperature ranges between 15ºC and 28ºC in this part of Orange County.
Where can I rent a Middletown holiday house with great views?
If your idea of a relaxing break is one admiring pretty vistas without leaving the property, we'll help you book a holiday home rental you'll adore. Into views of historic areas? Stayz has houses in Middletown that offer exactly that.
Does Middletown have any weekend house rentals?
Browse our weekend rentals and prepare for a fun-filled few days away. Our tips for booking the perfect house in Middletown? Be flexible when searching and modify your dates until you find the holiday home rental that matches your needs.
Are there any pet-friendly house rentals in Middletown?
With our filter tool, finding a pet-friendly holiday home rental in Middletown is a walk in the park. Simply click on "Pets allowed" to see houses that feature extras to make your four-legged pal feel welcome, such as pet toys and fenced yards.
What are the top things to do in Middletown?
Orange County Fair Speedway, The Rock Sports Complex and Orange County Fairgrounds are top attractions that'll keep the whole family occupied in Middletown. There's nothing like travel to bring everyone together, so check out our holiday home rentals in this exciting destination.
Why should I book my holiday rental house with Stayz?
We take the hassle out of finding your perfect holiday home rental. Use our filters to fine-tune your search by property reviews, budget, amenities and more. Whatever your preference, you'll always get the entire property for you and whoever you're holidaying with. Plus, our cancellation policies offer peace of mind should your plans change. You'll get your money back if you cancel your booking within the timeframe specified by the property's cancellation policy.