Discover a selection of 223 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 $137 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 223 vacation rentals around Middletown. From 47 house rentals to 54 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a city-center property in Middletown?

Roll straight out of bed and stroll to those must-visit attractions. Or simply get caught up in the thrilling energy of city living! Spend your next vacay in the middle of the main streets, with a city centre vacation rental. Vrbo has 20 centrally located rental homes available. Searching for a different setting? See if any of our other properties tickle your fancy. Our options here include:

  • 14 rural vacation rentals.
  • 11 resort vacation rentals.
  • 7 riverside vacation rentals.

Can I rent a hotel in Middletown?

Whether you're searching for a place that greets its guests with an icy bottle of Champagne and a cheese platter or you're simply after a comfy bed to conk out in after a long day of sightseeing, we've got the perfect hotel for you. Currently, there are 61 options available on Vrbo. Prices start at $44 a night. If that doesn't fit with your posse's style, we have a range of other property types to select from, such as:

  • House: 49 vacation homes. Prices start from $40 per night.
  • Apartment: 22 vacation homes. Prices start from $49 per night.
  • Condo: 18 vacation homes. Prices start from $123 per night.

Can I stay in Middletown in a large group?

There's nothing more memorable than exploring somewhere completely new with close friends and family. And the best news is Vrbo has some places suitable for big groups. House vacation homes are the favored option for big groups of guests, with 9 listed here. If you're wanting to stay in a big group, the property options that can meet your needs include:

  • If yours is a crew of 6, we have 83 vacation homes suitable for that size. Book a night from just $71.
  • Need a rental property for 8 people? We have 78 that will serve you well. The starting price is $98 per night.
  • Looking for places for rent to suit 5 guests? You'll be delighted to know we have 33 that'll be perfect. You can grab one for as little as $98 a night.

You and all your mates will be well looked after when you arrange your Middletown travels with us!