Discover a selection of 1,000 holiday rentals in Middletown, NY, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 224 per night, and houses and cabins are popular options for a stay in Middletown. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Middletown
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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, Vrbo 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

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.

Can I find a vacation rental around Middletown?

Yes, our 2021 property listings offer a large selection of 938 vacation rentals near Middletown. From 706 houses to 137 cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Middletown for a holiday or a weekend are on Vrbo.

Can I rent Houses in Middletown?

Yes, of course. Vrbo UK has 706 Houses in Middletown. Our other popular types of vacation rentals in Middletown include:

  • Cabins: 137 rentals available
  • Bungalows: 114 rentals available
  • Cottages: 114 rentals available

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

Can I find a vacation rental with pool in Middletown?

Yes, you can select your preferred vacation rental with pool among our 281 vacation rentals with pool available in Middletown. Please use our search bar to access the selection of vacation rentals available.