Photo by Vincent Ramundo

Middletown rentals with pool

We found 702 rentals with pool — 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

How much does it cost to stay in a holiday home with a pool in Middletown?
Indoor or outdoor pool, one bedroom or many, low season or peak season — how much you'll pay for your stay in Middletown is influenced by a wide array of variables. But the one enduring aspect? Our holiday homes with a pool are where precious family memories are made. To find an escape that works with your budget, narrow your search results by price. You can also use our "Discounts" filter to find properties that offer savings on longer stays.
When is the best time to book a holiday home with a pool in Middletown?
Our holiday homes with a pool in Middletown see the greatest influx of bookings in August. Expect average temperatures of between 15ºC (15ºC) and 28ºC (28ºC) if you're visiting this corner of Orange County then. If there's limited availability in August, explore possibilities in the month before or after.
What holiday homes with a pool in Middletown have nice views?
If your perfect getaway involves poolside activities and fascinating vistas, you'll discover Middletown holiday homes with a pool that provide just that. Book one with views of historic areas and dive deep into an unforgettable holiday experience.