Discover a selection of 1,000 vacation rentals in Middletown, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $100 per night, and houses and cottages are popular options for a stay in Middletown. Either way, you'll find a rental for everyone's needs.
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Destination guide

Head to the friendly city of Middletown

Enjoy the area's churches, architecture and festivals and make a vacation rental your home during your stay in Middletown. This welcoming city allures visitors with its shopping and restaurants. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities

Activities and attractions in Middletown

Are you looking for top things to see and do while you're in the area? Venture out of your cozy vacation rental and experience everything that Middletown has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Orange County Fairgrounds (1.5 mi / 2.4 km)
  • Soons Orchards (3.1 mi / 4.9 km)
  • Goshen Historic Track (5.9 mi / 9.5 km)
  • Castle Fun Center (9.1 mi / 14.6 km)
  • Warwick Valley Winery and Distillery (10.7 mi / 17.2 km)
  • Scenic Farms Golf Course (11 mi / 17.8 km)
Natural features

Exploring the natural landscape of Middletown

Whether you're looking for adventure or just want to spend some time taking in the scenery, Middletown is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Thomas Bull Memorial Park (8 mi / 12.9 km)
  • The Rock Sports Complex (10.1 mi / 16.3 km)
  • Pine Island Town Park (10.6 mi / 17.1 km)
  • Frederick Franck's Pacem in Terris (14.1 mi / 22.7 km)
  • Arrow Park Lake and Lodge (16.7 mi / 26.9 km)
  • Mary H Harriman Memorial Park (17.1 mi / 27.6 km)
How to get there

Transportation options to and around Middletown

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 17.7 mi (28.5 km) from the city center.

How many vacation rentals are available around Middletown, NY?

Our 2020 property listings offer a large selection of 859 vacation rentals around Middletown. From 561 house rentals to 107 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Middletown?

Vrbo offers a large selection of vacation rentals near lovely places in Middletown. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Paramount Theatre: 221 vacation rentals
  • Orange County Fair Speedway: 212 vacation rentals
  • Orange County Fairgrounds: 205 vacation rentals
  • Orange Regional Medical Center: 219 vacation rentals
  • Mountain Creek Waterpark: 79 vacation rentals

But there are many other points of interest around Middletown listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Middletown?

Yes, of course. Vrbo has 561 Houses in Middletown. Our other popular types of vacation rentals in Middletown include:

  • Cottages: 107 rentals available
  • Bungalows: 107 rentals available
  • Condos/Apartments: 69 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Farmhouses and more.

Can I find a vacation rental with pool in Middletown?

Yes, you can select your preferred vacation rental with pool among our 252 vacation rentals with pool available in Middletown. Please use our search bar to access the selection of vacation rentals available.

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