Discover a selection of 141 vacation rentals in Middletown, PA 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 kitchens. Prices start at $84 per night, and houses and condos are popular options for a stay in Middletown. Either way, you'll find a rental for everyone's needs.
Destination guide

Time travel back to the 1700s with a Middletown vacation

Turn back the clocks, or maybe just stop them altogether. Founded in 1755, handsome Middletown is Dauphin County's oldest community, and life here is so laid-back you'll never want to return to the 21st century. A Middletown vacation rental is about strolling streets lined with gorgeous old buildings, taking rides on the old railroad, setting out on excursions to historic locations like Gettysburg and Harrisburg, or gorging on chocolate over at Hershey's. Many of the historic properties are very beautiful, and your Middletown vacation rental might even end up being in one of them.

Things to do

Long mustaches and cutlasses strictly optional

A Middletown vacation rental is the perfect opportunity to load up on some history. Gettysburg and the Civil War Museum in Harrisburg are both within cannon-firing distance, while the Middletown and Hummelstown railroad offers up train rides in old-fashioned cabooses, and themed events including Dillinger-esque train robberies. And if younger travelers aren't feeling so enthusiastic about the history lessons, you've still got an ace up your sleeve, courtesy of Hershey's chocolate. Just a 15-minute drive away is all the candy-related fun little hearts could desire, including chocolate tasting, tours, and a theme park with rides.


One man's junk is another man's treasure

She's a good-looking ol' town, is Middletown. And it's not just the architecture that's got a vintage charm all of its own. Saturday's Market is a giant flea/farmers' market, and you can easily spend all morning there if you're in the mood. From antiques to fresh food to books to furniture, there's bound to be a bargain here if you can only find it. When you've packed the car out with just about all the 1960s typewriters and ceramic ashtrays you can carry, head for a little R&R at the local winery and brewery, with tastings, food, and live music.


Regular as your great-uncle's pocket watch

Anywhere as venerable as Middletown is bound to do things by the book, so it should come as no surprise that you'll get all 4 seasons, pretty much as they ought to be. Winter is cold, with heavy snowfalls a distinct possibility, and springs can be very mild. Historically this area was big on agriculture, and no doubt the hot, humid summers and occasional thunderstorms helped to keep those crops growing tall. As for fall, it can still be nice and warm, and can make a lovely time for a Middletown vacation rental.

Natural features

Fantastic fowl and where to find them

Laid in stately fashion along the banks of the Susquehanna river, Middletown is on the western edge of Dauphin County. The terrain's mostly pretty agricultural, with a fair bit of industry dotted around. While all this means it's not exactly the last great wilderness, there are 2 decent-sized conservation areas in the county. Both are dominated by big hardwood trees, and support healthy populations of deer, black bear, and squirrels. Birdwatchers will have their eyes open for turkey, grouse, warblers, and the hawks that migrate across each year.

How to get there

Transportation options to and around Middletown

Fly into Harrisburg, PA (MDT-Harrisburg Intl.), the closest airport, located 1.8 mi (2.8 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Harrisburg, PA (HAR-Capital City), which is 7.1 mi (11.4 km) away.

If you'd rather travel by train, the main station serving the city is Middletown Station.

How many vacation rentals are available around Middletown, PA?

Our 2020 property listings offer a large selection of 141 vacation rentals around Middletown. From 46 house rentals to 55 condo and apartment 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:

  • Middletown & Hummelstown Railroad: 307 vacation rentals
  • Penn State Harrisburg: 306 vacation rentals
  • Vineyard at Hershey: 312 vacation rentals
  • Doc's Family Fun Center: 312 vacation rentals
  • Saturday's Market: 310 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 46 Houses in Middletown. Our other popular types of vacation rentals in Middletown include:

  • Condos/Apartments: 55 rentals available
  • Villas: 7 rentals available
  • Cabins: 5 rentals available

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

Can I find a vacation rental with pool in Middletown?

Yes, you can select your preferred vacation rental with pool among our 45 vacation rentals with pool available in Middletown. Please use our search bar to access the selection of vacation rentals available.