Destination guide

Head to the friendly city of Middletown

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


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 cosy holiday 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 centre:

  • 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 centre:

  • 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

Transport 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 centre.

How many holiday rentals are available around Middletown?

Our 2020 accommodation listings offer a large selection of 910 holiday lettings around Middletown. From 589 houses to 103 bungalows, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

Can I rent a mountain-view property in Middletown?

We all adore a room with a view. But if you're longing for views that'll leave you feeling like you're on cloud nine, you'll have to head for the hills. HomeAway has no less than 244 alpine getaway rentals available. Open to other ideas? HomeAway has oodles more options to look through, including:

  • 217 rural holiday accommodation options.
  • 144 water-view holiday accommodation options.
  • 122 lakefront holiday accommodation options.

Can I rent a house in Middletown?

Instead of staying in a cookie-cutter, chain hotel room this holiday, you could rent a whole house. You'll feel like part of the neighbourhood before you know it! There are 564 options currently available on HomeAway. Prices begin at £35 per night. Or perhaps you'd rather one of the area's other sought-after self-catering accommodation options, like:

  • Hotel: 89 self-catering accommodation options. Prices start from £38 per night.
  • Condo: 57 self-catering accommodation options. Prices start from £82 per night.
  • Cabin: 53 self-catering accommodation options. Prices start from £69 per night.

Can I stay in Middletown in a large group?

The recipe for a wonderful getaway is catching up with loved ones in a fantastic new place. If you'll be travelling with a big group, HomeAway has options for you. Why not take a peek at the 110 house holiday rentals listed here? They're the top choice for large groups of visitors. If you're hoping to travel in a big group, the holiday rental options that can meet your needs include:

  • Searching for rentals that can house 6 guests? We have 206 that will suit. Prices begin from just £61 per night.
  • Require a holiday property for 8 guests? We have 150 that will be perfect. The starting price is £63 a night.
  • Trying to find rental properties catering to 10 guests? You'll be thrilled to know we have 92 that'll be perfect. You can secure one from just £76 a night.

You and all your mates will be well catered to when you book your Middletown holiday through us!

Where are the cheapest holiday rentals in Middletown?

Give the flick to dull cookie-cutter chain-hotel rooms! Appreciate the ease of living like one of the locals in a value-for-money holiday rental instead. Have a look at the unique options that can be booked now on HomeAway. Booking a holiday rental in or around Highland Lakes is a good way to avoid breaking the bank. HomeAway have 8 options and the average cost is £189 per night.

Explore destinations around Middletown