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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, HomeAway 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?

Our 2020 vacation rental listings offer a large selection of 920 house rentals around Middletown. From 592 Houses to 108 Cabins, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Middletown is on HomeAway.

What are the popular points of interest near where I can stay when travelling to Middletown?

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

  • Orange County Fairgrounds: 207 home rentals
  • Paramount Theatre: 230 home rentals
  • Orange County Fair Speedway: 219 home rentals
  • Woodbury Common Premium Outlets: 207 home rentals
  • Witness Monument: 207 home rentals

But there are many other points of interest around Middletown listed on HomeAway 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. HomeAway has 592 Houses in Middletown. Our other popular types of vacation rentals in Middletown include:

  • Cabins: 108 lodging choices
  • Bungalows: 108 lodging choices
  • Cottages: 108 lodging choices

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

Can I find a vacation rental with pool in Middletown?

Yes, you can select your preferred vacation rental with pool among our 303 vacation homes with pool available in Middletown.